Potassium Carbonate → HCID 58271194, compound

HRID 1665246Notes

Reaction equation

HRID 1665246 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].[CH3:10][O:11][C:12](=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19]Br)[CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:10][O:11][C:12](=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][O:8][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([F:9])[CH:4]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 517981Methyl 3-(bromomethyl)benzoateHCID 27791534-Bromo-3-fluorophenol

Product 1

HCID 58271194HCID 58271194, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-bromo-3-fluorophenol (18.34 g, 96 mmol), 3-bromomethylbenzoic acid methyl ester (20 g, 87.3 mmol), potassium carbonate (13.3 g, 96 mmol), and acetone (300 mL) was heated to reflux overnight, followed by cooling to room temperature and filtered. The filtrate was evaporated. The solid was washed with water and cold MeOH to give 3-(4-bromo-3-fluoro-phenoxymethyl)-benzoic acid methyl ester, 28 g (72%). LC-MS (ES) calculated for C15H12BrFO3, 338; obsd 339 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. washThe solid was washed with water and cold MeOH

Sources & evidence

ORD record
ord-e0444c95718f425aae4e6747da9d4055
Source dataset
uspto-grants-2011_10
Patent number
US08039495B2

Reaction notes

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