Water → 5-bromo-2-nitro-n-phenylaniline

HRID 1966426Notes

Reaction equation

HRID 1966426 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.C(N(C(C)C)CC)(C)C.[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CN1C(=O)CCC1>[C:22]1([NH:21][C:4]2[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=2[N+:8]([O-:10])=[O:9])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6115AnilineHCID 81531DiisopropylethylamineHCID 27833624-Bromo-2-fluoro-1-nitrobenzene

Product 1

HCID 2386965-bromo-2-nitro-n-phenylanilineYield 90%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 4-bromo-2-fluoro-1-nitrobenzene (1.0 g, 4.58 mmol) and diisopropyl ethylamine (1.1 mL, 6.87 mmol) in NMP (10 mL) was added aniline (0.51 g, 5.49 mmol). The solution was stirred for 14 h to which was slowly added H2O (5 mL). The resulting yellow precipitate was filtered, washed with 5 mL of water, dried (high vacuum, 14 h) to furnish N-phenyl-5-bromo-2-nitrobenzenamine (1.2 g), 90% yield. 1H NMR (500 MHz, CDCl3): δ 6.92 (dd, J=2 Hz, 1H), 7.35 (m, 5H), 7.51 (m, 1H) 8.11 (d, J=9.0 Hz, 1H), 9.55 (bs, 1H).

Workup

  1. filtrationThe resulting yellow precipitate was filtered
  2. washwashed with 5 mL of water
  3. customdried (high vacuum, 14 h)

Sources & evidence

ORD record
ord-8c04598307cb4889bf25c1ada1e00a5e
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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