1,2-Dichloroethane → Benzamide, 4-bromo-2-fluoro-N-methyl-

HRID 1453004Notes

Reaction equation

HRID 1453004 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([F:11])[CH:3]=1.CN.C(Cl)CCl.[CH2:18]([N:20](CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:20][CH3:18])=[O:7])=[C:4]([F:11])[CH:3]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6329MethylamineHCID 8471TriethylamineHCID 3026814-Bromo-2-fluorobenzoic acid

Product 1

HCID 24694329Benzamide, 4-bromo-2-fluoro-N-methyl-Yield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-bromo-2-fluorobenzoic acid (0.8 g, 3.7 mmol), methylamine (3.65 mL, 7.3 mmol), EDC (1.4 g, 7.3 mmol), triethylamine (1.0 mL, 7.3 mmol) dissolved in CH2Cl2 (15 mL) was stirred under N2 for 24 h. The reaction mixture was partitioned between 1N HCl and EtOAc. The organic layers were washed with saturated NaHCO3, brine, dried over dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (40% EtOAc in hexanes) to give the title compound as a white solid (0.27 g, 32%). 1H NMR (CDCl3): δ 3.03 (d, 3H, J=6.0 Hz), 6.68 (br s, 1H), 7.32 (d, 1H, J=11.3 Hz), 7.42 (d, 1H, J=10.2 Hz), 8.01 (t, 1H, J=8.5 Hz).

Workup

  1. customThe reaction mixture was partitioned between 1N HCl and EtOAc
  2. washThe organic layers were washed with saturated NaHCO3, brine
  3. customdried
  4. dry with materialover dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a12e54a37d31420c9abc5f60c93d8bac
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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