2-(4-bromo-2-chlorophenyl)acetic acid synthesis
- Product Name:2-(4-bromo-2-chlorophenyl)acetic acid
- CAS Number:916516-89-7
- Molecular formula:C8H6BrClO2
- Molecular Weight:249.49
67197-54-0
916516-89-7
In a round-bottomed flask, 2-chloro-4-bromophenylacetonitrile (19.0 g, 82.4 mmol, 1.0 eq.) was dissolved in water (196 mL), followed by the addition of potassium hydroxide (KOH, 23.1 g, 412 mmol, 5.0 eq.). The reaction mixture was heated to reflux and stirred for 12-18 hours. After completion of the reaction, it was cooled to room temperature and washed with ethyl acetate (EtOAc) to remove organic impurities. The aqueous phase was acidified with 2N hydrochloric acid to pH < 2 and subsequently extracted with ethyl acetate (150 mL x 3). The organic phases were combined, washed with saturated sodium chloride solution (brine), dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure to afford 2-(4-bromo-2-chlorophenyl)acetic acid (S3) as brown crystals (19.1 g, 93% yield). The product characterization data were in agreement with literature reports. [20]
67197-54-0
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916516-89-7
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Yield: 93%
Reaction Conditions:
with potassium hydroxide in waterReflux;
Steps:
2-(4-bromo-2-chlorophenyl)acetic acid (S3)
In a flask, water (196 mL) was added to 2 (19.0 g, 82.4 mmol, 1.0 equiv.) and then KOH (23.1 g, 412 mmol, 5.0 eq,) was added. The mixture was allowed to stir at reflux for 12-18 h, cooled, washed with EtOAc to remove impurities, then acidified with 2 N HCl and extracted with EtOAc (150 mL x 3). The combined organics were washed with brine, dried over MgSO4, filtered, and then reduced to yield S3 as tan crystals (19.1 g, 93 %). Characterization data was identical to previous reports.[20]
References:
Koval, Alexander B.;Wuest, William M. [Tetrahedron Letters,2016,vol. 57,# 3,p. 449 - 451]
185315-48-4
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916516-89-7
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89720-77-4
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916516-89-7
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59748-90-2
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916516-89-7
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