ChemicalBook CAS DataBase List (R)-2-BROMO-1-(4-FLUOROPHENYL)ETHANOL

(R)-2-BROMO-1-(4-FLUOROPHENYL)ETHANOL synthesis

5synthesis methods

Product Name:(R)-2-BROMO-1-(4-FLUOROPHENYL)ETHANOL
CAS Number:1097211-38-5
Molecular formula:C8H8BrFO
Molecular Weight:219.0509

403-29-2 Synthesis

403-29-2
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1097211-38-5
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Yield:1097211-38-5 100%

Reaction Conditions:

with dimethylsulfide borane complex;(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole in tetrahydrofuran at 20;Inert atmosphere;stereoselective reaction;

Steps:

4.3.6. (1R)-2-bromo-1-(4-fluorophenyl)ethan-1-ol (7a) and (1S)-2-bromo-1-(4-fluorophenyl)ethan-1-ol (7b)

Reaction was carried out in dry conditions under argon atmosphere. For the synthesis of 7a, 2 M THF solution of BH₃·Me₂S (1.15 mL, 2.30 mmol) was added to a solution of (R)-(+)-2-methyl-CBS-oxazaborolidine catalyst (64 mg, 0.23 mmol) in anhydrous THF (2 mL). The mixture was stirred for 10 min and a solution of 2-bromo-1-(4-fluorophenyl)ethan-1-one 3 (500 mg, 2.30 mmol) in anhydrous THF (4 mL) was added dropwise. Reaction proceeded at room temperature overnight. Reaction mixture was quenched with methanol, solvent evaporated to dryness and distilled water (15 mL) added. The product was extracted with CH₂Cl₂ (3 × 30 mL), collected organic layers dried over Na₂SO₄ and solvent evaporated to dryness. 7a was purified by a silica gel column chromatography (hexane/ethyl acetate 6:1) and obtained as colourless oil (503 mg, 100%). The ee>99% of 7a was determined by chiral HPLC (200/4 Nucleodex beta-PM Column, Macherey-Nagel, Germany, Method: 0.1% TEAA in H₂O: methanol 55: 45, 30 min, flow 0.7 mL/min, λ = 254 nm, retention time 19.5 min). [α]_D²⁰ = -28 (c = 1, EtOAc). 7b was synthesized following the same procedure using (S)-(-)-2-methyl-CBS-oxazaborolidine catalyst. The ee>99% was determined by chiral HPLC (retention time 18.0 min).

References:

Drai, Tonko;Molanov, Kreimir;Sachdev, Vinay;Malnar, Martina;Heimovi, Silva;Patankar, Jay V.;Obrowsky, Sascha;Levak-Frank, Sanja;Habu, Ivan;Kratky, Dagmar [European Journal of Medicinal Chemistry,2014,vol. 87,p. 722 - 734]

405-99-2 Synthesis

405-99-2
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1097211-38-5
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1234372-12-3
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References

95895-33-3
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1097211-38-5
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References

332-42-3
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$15.00/1g

1097211-38-5
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References

7589-27-7
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1097211-38-5
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References