Hydrochloride methanol → 4-Bromo-beta,beta-dimethylbenzeneethanol

HRID 338291Notes

Reaction equation

HRID 338291 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:19])([CH3:18])[CH2:9][O:10][Si](C(C)(C)C)(C)C)=[CH:4][CH:3]=1.Cl.CO>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:19])([CH3:18])[CH2:9][OH:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 21986021(2-(4-Bromophenyl)-2-methylpropoxy)(tert-butyl)dimethylsilane

Product 1

HCID 128051244-Bromo-beta,beta-dimethylbenzeneethanolYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of [2-(4-bromophenyl)-2-methylpropoxy](tert-butyl)dimethylsilane (500 mg, 1.46 mmol) in MeOH (5 mL) was added dropwise HCl/MeOH (5 mL) at room temperature. The reaction mixture was stirred at room temperature for 2 hours. The reaction was concentrated to give a crude residue, which was purified by column chromatography to give the title compound (250 mg, 75%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.38 (d, 2H), 7.19 (d, 2H), 3.50 (s, 2H), 1.23 (s, 6H).

Workup

  1. concentrationThe reaction was concentrated
  2. customto give a crude residue, which
  3. customwas purified by column chromatography

Sources & evidence

ORD record
ord-f9a1d7e1d5d14214af3fc8aa3449cf07
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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