4-Fluoro-3-nitroaniline → 326901-29-5

HRID 605262Notes

Reaction equation

HRID 605262 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[Br:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1.C(N(C(C)C)CC)(C)C>ClCCl>[Br:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([NH:6][C:5]2[CH:7]=[CH:8][C:2]([F:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=2)=[O:18])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 677684-Fluoro-3-nitroanilineHCID 685154-Bromobenzoyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 771890326901-29-5Yield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 4-Fluoro-3-nitro aniline (0.5 g, 3.2 mmol), 4-bromobenzoyl chloride (0.702 g, 3.2 mmol), diisopropylethylamine (0.56 ml, 3.2 mmol) in dichloromethane (10 mL) was stirred at room temperature for 2 hr. The mixture was diluted with dichloromethane (50 mL) and washed with 10% sodium bicarbonate and 10% sodium chloride, then dried over anhydrous sodium sulfate, filtered and concentrated under vacuum giving the title compound as a yellow solid (0.89 g, 82%).

Workup

  1. washwashed with 10% sodium bicarbonate and 10% sodium chloride
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9b6ef7b687a744e0a12989f97a40e672
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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