Benzyl Bromide → HCID 53694565, compound

HRID 736453Notes

Reaction equation

HRID 736453 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+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O>[CH2:18]([O:11][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:10][C:6]=1[C:7]([O:9][CH2:7][C:6]1[CH:10]=[CH:2][CH:3]=[CH:4][CH:5]=1)=[O:8])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 676585-Fluorosalicylic acid

Product 1

HCID 53694565HCID 53694565, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 10.5 g (67.3 mmol) 5-fluoro-2-hydroxybenzoic acid and 37.1 g (269 mmol) fine mesh K2CO3 in 250 mL of acetone was added 18.0 μL (151.2 mmol) benzyl bromide and the resulting mixture was refluxed for 5 h. After cooling to room temperature, the solids were filtered off, the filtrate was concentrated, loaded onto a silica gel column, and eluted with EtOAc/hexanes to provide 3-1 as a white solid. Data for 3-1: 1HNMR (500 MHz, CDCl3) δ 7.55 (m, 1H), 7.4-7.3 (m, 10H), 7.1 (m, 1H), 6.95 (m, 1H), 5.35 (s, 2H), 5.1 (s, 2H) ppm.

Workup

  1. temperaturethe resulting mixture was refluxed for 5 h
  2. filtrationthe solids were filtered off
  3. concentrationthe filtrate was concentrated
  4. washeluted with EtOAc/hexanes

Sources & evidence

ORD record
ord-cb43da5b7696451d91631026556d1945
Source dataset
uspto-grants-2009_09
Patent number
US07595337B2

Reaction notes

Loading…