Benzyl Bromide → Benzyl 2-(benzyloxy)-4-chlorobenzoate

HRID 660820Notes

Reaction equation

HRID 660820 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([OH:11])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C>[CH2:18]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][C:4]=1[O:11][CH2:6][C:5]1[CH:9]=[CH:10][CH:2]=[CH:3][CH:4]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 787824-Chlorosalicylic acid

Product 1

HCID 66989997Benzyl 2-(benzyloxy)-4-chlorobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a suspension of 4-chloro-2-hydroxybenzoic acid (10.0 g, 57.9 mmol) and K2CO3 (20.8 g, 151 mmol) in DMF (115 mL) is added benzyl bromide (14.5 mL, 122 mmol) and the mixture is stirred at 85° C. for 7 h. The mixture is allowed to cool to RT and is partitioned between EtOAc and 1N HCl. The organic phase is washed with 1N HCl and brine then is dried over sodium sulfate. The solvent is removed under reduced pressure to give the title compound which is used directly in the next step.

Workup

  1. temperatureto cool to RT
  2. customis partitioned between EtOAc and 1N HCl
  3. washThe organic phase is washed with 1N HCl and brine
  4. dry with materialthen is dried over sodium sulfate
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-659d596c22aa46e88a433d01416c2a91
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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