Ethanol → Methyl 4-fluoro-3-[(4-fluorophenyl)methoxy]benzoate

HRID 878682Notes

Reaction equation

HRID 878682 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[OH:12].Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].C(O)C>O>[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:12][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 120168924-Fluoro-3-hydroxy-benzoic acid methyl ester

Product 1

HCID 86725638Methyl 4-fluoro-3-[(4-fluorophenyl)methoxy]benzoateYield 67.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Charge methyl 4-fluoro-3-hydroxybenzoate (519 mg, 3.05 mmol), 4-(bromomethyl)-1-fluorobenzene (577 mg, 3.05 mmol), K2CO3 (843 mg, 6.10 mmol) and ethanol (10 mL) to a flask. The mixture was then stirred at room temperature overnight. Water was added to the reaction mixture at 0° C., filtered, and the solid dried and purified by flash column chromatograph to give 571 mg of the title compound (67%). 1H NMR (400 MHz, CDCl3): δ 3.90 (3H, s), 5.13 (2H, s), 7.06-7.15 (3H, m), 7.41-7.45 (2H, m), 7.63-7.67 (1H, m), 7.71 (1H, dd, J=2.0 Hz, 8.4 Hz).

Workup

  1. filtrationfiltered
  2. customthe solid dried
  3. custompurified by flash column chromatograph

Sources & evidence

ORD record
ord-47ba4a75e0f246c88ab73f01d8b713f7
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

Loading…