5-Bromosalicylic acid → Benzyl 2-(benzyloxy)-5-bromobenzoate

HRID 1623620Notes

Reaction equation

HRID 1623620 reaction equation
C([O-])([O-])=O.[K+].[K+].[Br:7][C:8]1[CH:9]=[CH:10][C:11]([OH:17])=[C:12]([CH:16]=1)[C:13]([OH:15])=[O:14].Br[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([O:17][CH2:13][C:12]2[CH:16]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[C:12]([CH:16]=1)[C:13]([O:15][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:14]

Participants

5

Reactant 3

HCID 69725-Bromosalicylic acidHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 17750009Benzyl 2-(benzyloxy)-5-bromobenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

K2CO3 (701 mg, 5.00 mmol) was added to a stirred solution of 5-bromo-2-hydroxybenzoic acid (434 mg, 2.00 mmol) in acetone (30 ml), followed by the addition of (bromomethyl)benzene (855 mg, 5.00 mmol). The mixture was refluxed for 12 h and then cooled to room temperature. The mixture was filtered and the filtrate was concentrated to a yellow solid. Flash chromatography over silica gel, using 1:10 ethyl acetate-petroleum ether yielded the title compound as a pure, white powder. 700 mg.

Workup

  1. temperatureThe mixture was refluxed for 12 h
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated to a yellow solid

Sources & evidence

ORD record
ord-2830dd81be26495da4e8088948d3d793
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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