4-Bromo-beta,beta-dimethylbenzeneethanol → HCID 10013947, compound

HRID 1852441Notes

Reaction equation

HRID 1852441 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:12])([CH3:11])[CH2:9][OH:10])=[CH:4][CH:3]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:12])([CH3:11])[CH:9]=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 128051244-Bromo-beta,beta-dimethylbenzeneethanolHCID 178418287HCID 178418287, compound

Product 1

HCID 10013947HCID 10013947, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(4-bromophenyl)-2-methylpropan-1-ol (10 g, 44 mmol) in dichloromethane (80 mL) was added PCC (14 g, 65 mmol) in portions at 0° C. The resulting solution was stirred at ambient temperature for 16 hours, and then filtered and concentrated in vacuo. The crude residue was purified by MPLC on silica gel (eluting with 1-2% EtOAc/hexane) to afford the title compound as an off-white solid. 1H NMR (300 MHz, CDCl3) δ 9.49 (s, 1H), 7.52 (d, J=6.3 Hz, 2H), 7.17 (d, J=6.3 Hz, 2H), 1.43 (s, 6H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe crude residue was purified by MPLC on silica gel (eluting with 1-2% EtOAc/hexane)

Sources & evidence

ORD record
ord-df0e95e517f14bf18908c7018e557921
Source dataset
uspto-grants-2015_02
Patent number
US08962608B2

Reaction notes

Loading…