Water → alpha-Bromo-2-chlorobenzeneacetic acid

HRID 1087616Notes

Reaction equation

HRID 1087616 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1C=O.Br[CH:11]([Br:13])Br.[OH2:14].[OH-].[K+].COCC[O:21][CH3:22]>>[Br:13][CH:11]([C:9]1[CH:8]=[CH:7][CH:6]=[CH:3][C:2]=1[Cl:1])[C:22]([OH:21])=[O:14]

Participants

6

Reactant 5

HCID 962Water2×HCID 5558BromoformHCID 69962-ChlorobenzaldehydeHCID 80711,2-Dimethoxyethane2×HCID 14797Potassium Hydroxide

Product 1

HCID 2774031alpha-Bromo-2-chlorobenzeneacetic acid

Procedure

A solution of 70.3 g of (2-chloro)benzaldehyde and 139 g of tribromomethane diluted in 50 ml of 1,2-dimethoxy ethane are added to a vigorously stirred mixture of 131 ml of water, 114 g of potassium hydroxide (titer 86%) and 50 ml of 1,2-dimethoxy ethane at a temperature of about -5° C. After 3 hours at about -5° C., 500 ml of water are added to the reaction mixture at a temperature lower than or equal to 0° C. then the temperature is allowed to rise to 10° C. and maintained there for 10 hours.

Workup

  1. customto rise to 10° C.
  2. temperaturemaintained there for 10 hours

Sources & evidence

ORD record
ord-4ffcbaaff1a0487c8240b396ba3e824f
Source dataset
uspto-grants-1991_07
Patent number
US05036156

Reaction notes

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