p-Bromochlorobenzene → HCID 53634461, compound

HRID 845217Notes

Reaction equation

HRID 845217 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=1.C([Li])CCC.[Br:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[O:19].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[Br:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]([OH:19])[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7806p-BromochlorobenzeneHCID 25517Ammonium ChlorideHCID 765833-BromobenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 53634461HCID 53634461, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of 4-bromochlorobenzene (20.0 g, 104 mmol) in 125 mL of dry tetrahydrofuran under nitrogen was cooled to -78° and 70 mL of 1.5M n-butyllithium in hexane was added dropwise over 20 minutes. After stirring another 10 minutes, 12.5 mL (104 mmol) of 3-bromobenzaldehyde was added dropwise and the reaction was stirred for another 10 minutes at -78°. Saturated aqueous ammonium chloride (100 mL) was added and the reaction was warmed to room temperature and extracted with 300 mL of ether. The ethereal layer was extracted with three 75 mL portions of 1M sodium bisulfite, 75 mL of 1M sodium hydroxide, 75 mL of water, and 75 mL of brine. The ether layer was dried over magnesium sulfate and the solvent removed to give 31.2 g of 3-bromo-4'-chlorobenzhydryl alcohol as a pale yellow solid. A portion was recrystallized from hexanes containing 5% ether to give white needles, m.p. 67°-68°. Calc. for C13H10Br C10: C, 52.47; H, 3.39; Br, 26.85; Cl, 11.91. Found: C, 52.25; H, 3.25; Br, 26.72; Cl, 12.09.

Workup

  1. stirringthe reaction was stirred for another 10 minutes at -78°
  2. extractionextracted with 300 mL of ether
  3. extractionThe ethereal layer was extracted with three 75 mL portions of 1M sodium bisulfite, 75 mL of 1M sodium hydroxide, 75 mL of water, and 75 mL of brine
  4. dry with materialThe ether layer was dried over magnesium sulfate
  5. customthe solvent removed

Sources & evidence

ORD record
ord-4b7a89302dc948ad92ef17e154c04e28
Source dataset
uspto-grants-1988_07
Patent number
US04757074

Reaction notes

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