Benzyl Bromide → HCID 53694565, compound

HRID 1623639Notes

Reaction equation

HRID 1623639 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:7][C:6]2[CH:10]=[CH:2][CH:3]=[CH:4][CH:5]=2)=[C:6]([CH:10]=1)[C:7]([O:9][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:8]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 676585-Fluorosalicylic acid

Product 1

HCID 53694565HCID 53694565, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 5-fluoro-2-hydroxybenzoic acid (468 mg, 3 mmol), potassium carbonate (1037 mg, 7.50 mmol) and (bromomethyl)benzene (1283 mg, 7.50 mmol) in acetone (60 ml) was stirred at 50° C. overnight. The mixture was cooled and filtered. The filtrate was concentrated and the crude product was purified by silica gel chromatography, eluting with hexane:ethyl acetate (10:1) to yield the title compound as a colourless oil. 860 mg.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customthe crude product was purified by silica gel chromatography
  5. washeluting with hexane:ethyl acetate (10:1)

Sources & evidence

ORD record
ord-b93857e4af0246e983bef702a4606b30
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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