Diethyl Ether → alpha-Bromo-2-chlorobenzeneacetic acid

HRID 1087615Notes

Reaction equation

HRID 1087615 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.[OH-:14].[K+].C([O:18][CH2:19]C)C>[Br-].C([P+](CCCC)(CCCC)CCCC)CCC.O>[Br:13][CH:11]([C:9]1[CH:8]=[CH:7][CH:6]=[CH:3][C:2]=1[Cl:1])[C:19]([OH:18])=[O:14]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 5558BromoformHCID 69962-ChlorobenzaldehydeHCID 14797Potassium Hydroxide

Product 1

HCID 2774031alpha-Bromo-2-chlorobenzeneacetic acid

Reagents, catalysts & solvents 2

HCID 76564Tetrabutylphosphonium bromideCatalystHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 141 g of (2-chloro)benzaldehye and 270 g of tribromomethane in 500 ml of ethyl ether is added to a solution of 270 g of potassium hydroxide and 34 g of tetrabutylphosphonium bromide in 800 ml of water. The mixture is stirred for 24 hours at 0° C.

Sources & evidence

ORD record
ord-0e981cbe0fba4a229bcde6faef4026e2
Source dataset
uspto-grants-1991_07
Patent number
US05036156

Reaction notes

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