Benzyl Bromide → 1-(Benzyloxy)-4-bromo-2-fluorobenzene

HRID 1509760Notes

Reaction equation

HRID 1509760 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC(CC)=O>[CH2:16]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[F:9])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27249814-Bromo-2-fluorophenol

Product 1

HCID 187574911-(Benzyloxy)-4-bromo-2-fluorobenzene

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

210.0 g (1.10 mol) of 4-bromo-2-fluorophenol are dissolved in 1.1 l of ethyl methyl ketone, and 175.0 g (1.27 mol) of potassium carbonate and 150.0 ml (1.26 mol) of benzyl bromide are added. The mixture is refluxed for 5 h and stirred at room temperature for 16 h. The batch is filtered, and the filtrate is concentrated to dryness. The crude product is crystallised from heptane at reduced temperature.

Workup

  1. temperatureThe mixture is refluxed for 5 h
  2. filtrationThe batch is filtered
  3. concentrationthe filtrate is concentrated to dryness
  4. customThe crude product is crystallised from heptane at reduced temperature

Sources & evidence

ORD record
ord-ba3525343e674790a9ae7d071c83f747
Source dataset
uspto-grants-2012_07
Patent number
US08211513B2

Reaction notes

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