4-Bromoaniline → HCID 43377434, compound

HRID 1846077Notes

Reaction equation

HRID 1846077 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Br:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1>C(Cl)Cl>[Br:14][C:15]1[CH:21]=[CH:20][C:18]([NH:19][C:4](=[O:5])[C:3]2[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:2]=2[F:1])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 78074-BromoanilineHCID 109765702-Fluoro-5-nitrobenzoyl chloride

Product 1

HCID 43377434HCID 43377434, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-fluoro-5-nitro-benzoyl chloride (1.1 g, 5.4 mmol) in 20 mL DCM was added dropwise to 4-bromoaniline (929 mg, 5.4 mmol), 0.905 mL TEA in 20 mL DCM. The mixture was stirred for 6 days, successively washed with satd. NaHCO3-solution and 2 M aq. HCl solution and dried with Na2SO4. After filtration and concentration i. vac. the subtitle compound was obtained. Yield: 1.57 g (86%). MS [M+H]+=339 (Br-isotope pattern); TLC: Rt=0.96 (silica gel, DCM:EtOH 9:1).

Workup

  1. washsuccessively washed with satd
  2. dry with materialNaHCO3-solution and 2 M aq. HCl solution and dried with Na2SO4
  3. filtrationAfter filtration and concentration i

Sources & evidence

ORD record
ord-48be548c7672438cb38a3dd2a4d64caa
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

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