Benzyl Bromide → Methyl 2-(4-benzyloxyphenyl)acetate

HRID 433671Notes

Reaction equation

HRID 433671 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:9]=1.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl>[CH3:18][O:17][C:15](=[O:16])[CH2:14][C:11]1[CH:10]=[CH:9][C:8]([O:7][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 2756645Methyl 2-(4-benzyloxyphenyl)acetateYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cesium carbonate (5.35 g, 16.4 mmol, 3.00 equivalents) was added to a solution of methyl 4-hydroxyphenylacetate (1.00 g, 6.02 mmol, 1.10 equivalents) and benzyl bromide (0.65 mL, 5.47 mmol, 1.00 equivalents) in dichloromethane (40 mL) at 0° C. The mixture was allowed to warm to room temperature and stirred vigorously overnight. The reaction was extracted with 1N hydrochloric acid (2×100 mL) and brine (100 mL). The organic portion was dried over sodium sulfate and the solvent removed in vacuo. The resulting oily solid was chromatographed on a 40S Biotage column (20% ethyl acetate/Hexanes) to give the title ester as a clear colorless oil (1.35 g, 96%). 1H NMR (400 MHz, CDCl3) δ 3.56 (s, 2H), 3.67 (s, 3H), 5.04 (s, 2H), 6.91-6.94 (d, 2H), 7.17-7.19 (d, 2H), 7.3-7.4 (m, 5H).

Workup

  1. extractionThe reaction was extracted with 1N hydrochloric acid (2×100 mL) and brine (100 mL)
  2. dry with materialThe organic portion was dried over sodium sulfate
  3. customthe solvent removed in vacuo
  4. customThe resulting oily solid was chromatographed on a 40S Biotage column (20% ethyl acetate/Hexanes)

Sources & evidence

ORD record
ord-2abffe3a140f4b348bdb331012a84f16
Source dataset
uspto-grants-2003_12
Patent number
US06667331B2

Reaction notes

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