1,4-Dibromobenzene → HCID 18507125, compound

HRID 2379683Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.C([Li])CCC.CCCCCC.[CH:20](=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=1>O1CCCC1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([CH:20]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=2)[OH:29])=[CH:3][CH:4]=1

Participants

Conditions

Temperature: -78 °C

Procedure

p-Dibromobenzene (7.08 g, 30.0 mmole) was added to 50 ml of anhydrous tetrahydrofuran under nitrogen and the slurry was cooled to -78° C. A solution of n-butyllithium in hexane (1.67M, 18.0 ml, 30 mmole) was added dropwise over 15 minutes. After stirring for ten minutes at -78° C., 3.8 ml (4.1 g, 30 mmole) of m-anisaldehyde was added dropwise over five minutes. After stirring for 15 minutes, the reaction was quenched with 10 ml of saturated aqueous ammonium chloride solution and was allowed to warm to room temperature. The reaction solution was diluted with 300 ml of diethyl ether and washed with three 50 ml portions of 1.0M aqueous sodium bisulfite, followed by 50 ml of 1.0 M sodium hydroxide, 100 ml of water, and 100 ml of saturated sodium chloride. After drying over magnesium sulfate, the solvent was removed to give 8.5 g (97%) of crude (4-bromophenyl)(3-methoxyphenyl)-methanol.

Workup

stirringAfter stirring for 15 minutes
customthe reaction was quenched with 10 ml of saturated aqueous ammonium chloride solution
temperatureto warm to room temperature
additionThe reaction solution was diluted with 300 ml of diethyl ether
washwashed with three 50 ml portions of 1.0M aqueous sodium bisulfite
dry with materialAfter drying over magnesium sulfate
customthe solvent was removed

Sources & evidence

ORD record: ord-43c7af8d70d0458eb470606df0d96bd1
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05364843

Reaction notes

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