Dimethylformamide → HCID 58271198, compound

HRID 1665247Notes

Reaction equation

HRID 1665247 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.[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+].CN(C=O)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])=[CH:3][C:4]=2[F:9])[CH:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 517981Methyl 3-(bromomethyl)benzoateHCID 27249814-Bromo-2-fluorophenol

Product 1

HCID 58271198HCID 58271198, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-bromo-2-fluorophenol (10 g, 52.36 mmol), 3-bromomethylbenzoic acid methyl ester (10.9 g, 47.6 mmol), potassium carbonate (9.9 g, 71.4 mmol), and DMF (100 mL) was stirred at room temperature over the weekend, followed by treatment with water. The precipitate was collected by filtration and washed with water and cold MeOH to give 3-(4-bromo-2-fluoro-phenoxymethyl)-benzoic acid methyl ester. LC-MS (ES) calculated for C15H12BrFO3, 338; found m/z 338 [M+H]+.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water and cold MeOH

Sources & evidence

ORD record
ord-2df6252e8ea14380a69766eabe040fc1
Source dataset
uspto-grants-2011_10
Patent number
US08039495B2

Reaction notes

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