p-Bromochlorobenzene → HCID 2757630, compound

HRID 893293Notes

Reaction equation

HRID 893293 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=1.C([Li])CCC.[CH:14](=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1>O1CCCC1.CCCCCC>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([CH:14]([OH:23])[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 7806p-BromochlorobenzeneHCID 115693-MethoxybenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 2757630HCID 2757630, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of 35.0 g (183 mmole) of 4-bromochlorobenzene in 300 ml of dry tetrahydrofuran was cooled to -78° C. under nitrogen and 115 ml (183 mmole) of 1.59 M n-butyllithium in hexane was added dropwise at a rate to maintain temperature below -60° C. After stirring an additional 15 minutes, 23.0 ml (183 mmole) of m-anisaldehyde was added dropwise and the reaction was stirred for 15 minutes. The reaction was quenched at -78° C. with saturated aqueous ammonium chloride and allowed to warm to room temperature. The reaction solution was diluted with 300 ml of diethyl ether and washed with three 150 ml portions of 1.0 M sodium bisulfite, followed by 100 ml of 1.0 M sodium hydroxide, 100 ml of water, and 50 ml of saturated sodium chloride. After drying over magnesium sulfate, the solvent was removed to give 45.2 g (99%) of crude 4-chloro-α-(3-methoxyphenyl)benzyl alcohol as a pale yellow oil.

Workup

  1. temperatureto maintain temperature below -60° C
  2. stirringthe reaction was stirred for 15 minutes
  3. customThe reaction was quenched at -78° C. with saturated aqueous ammonium chloride
  4. additionThe reaction solution was diluted with 300 ml of diethyl ether
  5. washwashed with three 150 ml portions of 1.0 M sodium bisulfite
  6. dry with materialAfter drying over magnesium sulfate
  7. customthe solvent was removed

Sources & evidence

ORD record
ord-08472abb45e149de8918a6b4eacea8c0
Source dataset
uspto-grants-1992_06
Patent number
US05124330

Reaction notes

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