Boron tribromide → 5-bromo-4-chloro-2-hydroxy-N-methyl-N-o-tolyl-benzamide

HRID 1848611Notes

Reaction equation

HRID 1848611 reaction equation
[Br:1][C:2]1[C:3]([Cl:21])=[CH:4][C:5]([O:19]C)=[C:6]([CH:18]=1)[C:7]([N:9]([CH3:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16])=[O:8].B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[C:3]([Cl:21])=[CH:4][C:5]([OH:19])=[C:6]([CH:18]=1)[C:7]([N:9]([CH3:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16])=[O:8]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 686036055-bromo-4-chloro-2-methoxy-N-methyl-N-o-tolyl-benzamide

Product 1

HCID 686026125-bromo-4-chloro-2-hydroxy-N-methyl-N-o-tolyl-benzamideYield 97.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of DCM (15.0 mL) containing 5-bromo-4-chloro-2-methoxy-N-methyl-N-o-tolyl-benzamide (2.75 g, 7.5 mmol) at −78° C., was added BBr3 (38.0 mL, 1M in DCM) dropwise. The mixture was gradually warmed to room temperature and stirred for 12 hrs. The mixture was concentrated to yield a solid which was washed by ether to give 5-bromo-4-chloro-2-hydroxy-N-methyl-N-o-tolyl-benzamide (2.6 g). MS: 353.8 (M+H)+; tR=2.50 min (method 1).

Workup

  1. concentrationThe mixture was concentrated
  2. customto yield a solid which
  3. washwas washed by ether

Sources & evidence

ORD record
ord-87fd714bccad451ab63eea02bf194062
Source dataset
uspto-grants-2015_02
Patent number
US08952161B2

Reaction notes

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