Benzyl Bromide → 1-(Benzyloxy)-3-chloro-2-fluorobenzene

HRID 17982Notes

Reaction equation

HRID 17982 reaction equation
[Cl:1][C:2]1[C:3]([F:9])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[K+]>COCCOC.O.C(OCC)C>[CH2:10]([O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[F:9])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 14797Potassium HydroxideHCID 27737123-Chloro-2-fluorophenol

Product 1

HCID 585926201-(Benzyloxy)-3-chloro-2-fluorobenzene

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 3-chloro-2-fluorophenol (1.5 g, 10.2 mmol), benzyl bromide (1.71 g, 10.0 mmol) and sodium carbonate (1.10 g, 10.38 mmol) in 20 mL ethylene glycol dimethyl ether and 10 mL H2O was stirred at rt for 36 h. The reaction mixture was charged with 20 mL 1N KOH and 50 mL diethyl ether. The organic layer was separated, washed with brine, dried over sodium sulfate, and concentrated in vacuo to afford the title compound as a white solid which was used without further purification. 1H NMR (CDCl3, 400 MHz) δ 5.16 (s, 2Hs) 6.86-7.03 (m, 3Hs) 7.31-7.48 (m, 5Hs).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-277708cca4ed4001a2f9f7525737ba56
Source dataset
uspto-grants-2010_06
Patent number
US07741324B2

Reaction notes

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