4-BROMO-2,6-DIFLUOROBENZYL ALCOHOL synthesis
- Product Name:4-BROMO-2,6-DIFLUOROBENZYL ALCOHOL
- CAS Number:162744-59-4
- Molecular formula:C7H5BrF2O
- Molecular Weight:223.01
4-Bromo-2,6-difluorobenzyl alcohol can be obtained by reducing the carboxyl group from 4-bromo-3,5-difluorobenzoic acid.
537013-51-7
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162744-59-4
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Yield:162744-59-4 95%
Reaction Conditions:
Stage #1:4-bromo-2,6-difluorobenzaldehyde with sodium tetrahydroborate in methanol;dichloromethane at 0; for 1 h;
Stage #2: with hydrogenchloride in methanol;dichloromethane;water for 0.5 h;
Steps:
82.a a) (4-bromo-2,6-difluoro-phenyl)methanol
To a stirred solution of 4-bromo-2,6-difluorobenzaldehyde (4.4 g, 19.9 mmol) in a 4: 1 mixture of CH2C12 and MeOH (100 mL) at 0 °C was added in one portion NaBH4 (829 mg, 21.9 mmol). The reaction mixture was stirred for 1 hour at 0 °C before being quenched by the careful addition of aqueous HC1 (1.0 M). After 30 min, the reaction was poured into water and extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2S04) and concentrated in vacuo to afford the title compound (4.24g, 95%) as a white solid. MS (ISP): 223.2 ([{81Br}M-HD, 221.2 ([{79Br}M-HD.
References:
F. HOFFMANN-LA ROCHE AG;HOFFMANN-LA ROCHE INC.;CECERE, Giuseppe;GALLEY, Guido;NORCROSS, Roger;PFLIEGER, Philippe;RAUBER, Etienne WO2016/30310, 2016, A1 Location in patent:Page/Page column 88; 89
183065-68-1
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162744-59-4
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461-96-1
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162744-59-4
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