Pyridine → 3-bromo-N-methoxy-N,2-dimethylbenzamide

HRID 1391792Notes

Reaction equation

HRID 1391792 reaction equation
[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].Cl.[CH3:13][NH:14][O:15][CH3:16].N1C=CC=CC=1.C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([N:14]([CH3:13])[O:15][CH3:16])=[O:6]

Participants

7

Reactant 5

HCID 1049PyridineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27355903-Bromo-2-methylbenzoic Acid

Product 1

HCID 218861973-bromo-N-methoxy-N,2-dimethylbenzamideYield 60.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromo-2-methyl benzoic acid (430 mg, 2.00 mmol) in anhydrous DCM, under nitrogen at ambient temperature was added N,O-dimethylhydroxylamine hydrochloride (215 mg, 2.20 mmol), pyridine (0.18 mL, 2.23 mmol) and CBr4 (662 mg, 2.00 mmol). Triphenyl phosphine (576 mg, 2.20 mmol) was added portion-wise over 10 min and the resulting mixture stirred at ambient temperature for 2.5 h. The reaction mixture then reduced under vacuum and purified by SPE (silica, 10 g cartridge) eluting with cyclohexane:EtOAc (gradient 99:1 to 4:1) to afford the title compound as a colourless oil (310 mg).

Workup

  1. custompurified by SPE (silica, 10 g cartridge)
  2. washeluting with cyclohexane

Sources & evidence

ORD record
ord-9e152bb29e3343deab3bc0366fd71775
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

Loading…