Water → 3-(4-Bromophenyl)-2-methylpropan-1-ol

HRID 1384218Notes

Reaction equation

B#B.[CH3:3][CH:4]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=1)[C:5](O)=[O:6].O.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[CH3:3][CH:4]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([Br:15])=[CH:13][CH:14]=1)[CH2:5][OH:6]

Participants

Conditions

Temperature: 0 °C

Procedure

Diborane (192 ml of a 1.0 M solution in THF) was added dropwise over 25 minutes to a solution of 2-methyl-3-(4-bromophenyl)propanoic acid (38.9 g) in THF (240 ml) at 0° C. The reaction mixture was stirred for 45 minutes at 0° C. and then allowed to warm to ambient temperature over 2 hours. Water (120 ml) was added followed by solid potassium carbonate (144 g) and then more water (80 ml). The reaction mixture was extracted with diethyl ether (3×250 ml), the combined organic layers were dried (MgSO4) and the solvent was evaporated to give 2-methyl-3-(4-bromophenyl)propanol as a yellow oil (37.4 g), mass spectrum (+ve CI): 248 (M+NH4)+.

Workup

temperatureto warm to ambient temperature over 2 hours
extractionThe reaction mixture was extracted with diethyl ether (3×250 ml)
dry with materialthe combined organic layers were dried (MgSO4)
customthe solvent was evaporated

Sources & evidence

ORD record: ord-af0d0cb88da74749bbb8d576a35f3c39
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06258817B1

Reaction notes

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