Benzyl Bromide → Ethyl 4-bromo-3-benzyloxybenzoate

HRID 908060Notes

Reaction equation

HRID 908060 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[OH:13].C([O-])([O-])=O.[K+].[K+].[CH:20]1[CH:25]=[CH:24][C:23]([CH2:26]Br)=[CH:22][CH:21]=1>CC(C)=O>[Br:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[O:13][CH2:26][C:23]1[CH:24]=[CH:25][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 12134897Ethyl 4-bromo-3-hydroxybenzoate

Product 1

HCID 12134898Ethyl 4-bromo-3-benzyloxybenzoateYield 84.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 4.5 g (18.4 mmol) of 6 and 4.1 g (30 mmol) of K2CO3 in 150 ml of acetone under Ar was added 3.4 g (20 mmol) of BnBr. The mixture was heated at reflux for 15 h, concentrated, then diluted with 100 ml of CH2Cl2, washed (water, 1 N HCl, and brine), and dried (Na2SO4). Concentration and chromatography (EtOAc/hexane) afforded 5.2 g (84%) of 7 (white solid): 1H NMR (300 MHz, CDCl3) δ 1.39 (t, J=7.2 Hz, 3 H), 4.37 (q, J=7.2 Hz, 2 H), 5.21 (s, 2 H), 7.39 (m, 3 H), 7.50 (in, 3 H), 7.63 ppm (m, 2 H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 15 h
  3. concentrationconcentrated
  4. additiondiluted with 100 ml of CH2Cl2
  5. washwashed (water, 1 N HCl, and brine)
  6. dry with materialdried (Na2SO4)
  7. concentrationConcentration and chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-e6579adaf95746bd8ab4401da316574b
Source dataset
uspto-grants-2011_09
Patent number
USRE042700E1

Reaction notes

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