N-bromobutanimide → 3-Bromo-4-fluoro-5-nitrobenzoic acid

HRID 1527457Notes

Reaction equation

HRID 1527457 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[F:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]=1[N+:19]([O-:21])=[O:20]>OS(O)(=O)=O>[Br:8][C:18]1[CH:17]=[C:13]([CH:12]=[C:11]([N+:19]([O-:21])=[O:20])[C:10]=1[F:9])[C:14]([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 679874-Fluoro-3-nitrobenzoic acid

Product 1

HCID 547587233-Bromo-4-fluoro-5-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
65 °C

Procedure

NBS (47.9 g, 0.268 mol) was added portion-wise to a solution of 4-fluoro-3-nitro-benzoic acid (41.5 g, 0.224 mol) in conc. H2SO4 (0.35 L). The reaction mixture was stirred for 5 h at 65° C. and then poured into ice-water (1.5 L). The precipitate was filtered off, washed twice with water (300 mL) and dried to give the title compound as a white solid. 1H-NMR (300 MHz, CDCl3): δ (ppm) 10.7 (s, br, 1H), 8.76 (m, 1H), 8.62 (m, 1H).

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed twice with water (300 mL)
  3. customdried

Sources & evidence

ORD record
ord-a88ed7ed9287477cbff5b9bdba6c4675
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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