Hydrochloric Acid → [3-(Benzyloxy)-4-bromophenyl]methanol

HRID 908061Notes

Reaction equation

HRID 908061 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([C:6](OCC)=[O:7])=[CH:4][C:3]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CC(C[AlH]CC(C)C)C.Cl>C(Cl)Cl>[Br:1][C:2]1[CH:12]=[CH:11][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14487Diisobutylaluminum hydrideHCID 12134898Ethyl 4-bromo-3-benzyloxybenzoate

Product 1

HCID 12134899[3-(Benzyloxy)-4-bromophenyl]methanolYield 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 3.35 g (10 mmol) of 7 in 25 ml of CH2Cl2 under Ar in a dry ice-acetone bath was slowly added 20 ml 1.0 M DIBAL with stirring. After stirring for 2 h, 20 ml of 1 N HCl and 50 ml of CH2Cl2 were added, and the mixture was stirred for 0.5 h, then washed (water and brine), and dried (Na2SO4). Concentration and chromatography (EtOAc/hexane) afforded 2.78 g (91%) of 8 (white solid): 1H NMR (300 MHz, CDCl3) δ 4.63 (d, J=5.7 Hz, 2 H), 6.83 (d, J=8.1 Hz, 1 H), 7.00 (s, 1 H), 7.40-7.33 (m, 3 H), 7.5-7.42 ppm (m, 3 H).

Workup

  1. stirringthe mixture was stirred for 0.5 h
  2. washwashed (water and brine)
  3. dry with materialdried (Na2SO4)
  4. concentrationConcentration and chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-2a59eb17566c4bdcb39a6577372a697f
Source dataset
uspto-grants-2011_09
Patent number
USRE042700E1

Reaction notes

Loading…