N-bromobutanimide → 2-Amino-5-bromo-3-fluorobenzoic acid

HRID 524076

Reaction equation

HRID 524076 reaction equation
[NH2:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:12]N1C(=O)CCC1=O>ClCCl>[NH2:1][C:2]1[C:10]([F:11])=[CH:9][C:8]([Br:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 5864082-Amino-3-fluorobenzoic acid

Product 1

HCID 404245972-Amino-5-bromo-3-fluorobenzoic acidYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-amino-3-fluorobenzoic acid (10.85 g, 70 mmol) in dichloromethane (175 mL) was added N-bromosuccinimide (12.46 g, 70 mmol), and the mixture was stirred at RT for 2 h. LCMS showed the reaction was completed. The precipitate was filtered and washed with dichloromethane (100 mL*3) to give the title compound (12.7 g, 78%) as a grey solid, which was directly used in the next step without further purification. MS (ES+) C7H5BrFNO2 requires: 233, 235. found: 232, 234 [M−H]−.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with dichloromethane (100 mL*3)

Sources & evidence

ORD record
ord-7dae895f0fd64c8e98396060340921c5
Source dataset
uspto-grants-2016_05
Patent number
US09340514B2

Linked notes

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