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

HRID 361436Notes

Reaction equation

HRID 361436 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

6

Reactant 4

HCID 962Water2×HCID 11430Potassium CarbonateHCID 6328200DiboronHCID 217141913-(4-Bromophenyl)-2-methylpropanoic acid

Product 1

HCID 217141993-(4-Bromophenyl)-2-methylpropan-1-olYield 102%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diborane (192 ml of a 1.0M 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 0C 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

  1. extractionThe reaction mixture was extracted with diethyl ether (3×250 ml)
  2. dry with materialthe combined organic layers were dried (MgSO4)
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-941cc1c5f6f1420c998fd6960cee9ee4
Source dataset
uspto-grants-1999_02
Patent number
US05866568

Reaction notes

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