Water → N-benzyl-4-bromo-2-fluoro-N-(2-hydroxyethyl)benzamide

HRID 886823Notes

Reaction equation

HRID 886823 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Br:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[C:22]([F:29])[CH:21]=1.O>O1CCCC1>[CH2:1]([N:8]([CH2:9][CH2:10][OH:11])[C:24](=[O:25])[C:23]1[CH:27]=[CH:28][C:20]([Br:19])=[CH:21][C:22]=1[F:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 4348BenzylethanolamineHCID 8471TriethylamineHCID 27340264-Bromo-2-fluorobenzoyl chloride

Product 1

HCID 60740299N-benzyl-4-bromo-2-fluoro-N-(2-hydroxyethyl)benzamideYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-benzylethanolamine (6.37 g, 42.1 mmol), triethylamine (8.81 ml, 63.2 mmol) in tetrahydrofuran (200 ml) was added under ice-cooling 4-bromo-2-fluorobenzoylchloride (10.0 g, 42.1 mmol), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the desired product (1.45 g, 98.0%) as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-e2bae3d1a5764e29a1548c6f01eaa99d
Source dataset
uspto-grants-2012_08
Patent number
US08247403B2

Reaction notes

Loading…