4-Bromoaniline → HCID 531936, compound

HRID 2056173Notes

Reaction equation

HRID 2056173 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Br:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.C(N(CC)C(C)C)(C)C>ClCCl>[Br:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][C:4](=[O:5])[C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=2[F:1])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 78074-BromoanilineHCID 98082-Fluorobenzoyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 531936HCID 531936, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-fluorobenzoyl chloride (5.82 g, 0.0367 mol) and 4-bromoaniline (6.31 g, 0.0367 mol) in anhydrous dichloromethane (150 mL) was cooled to 0° C. and N,N-diisopropylethylamine (5.21 g, 0.0407 mol) was added under nitrogen atmosphere dropwise. The resulting mixture was stirred at ambient temperature for 24 hours, concentrated and the residue partitioned between ethyl acetate (120 mL) and water (100 mL). The organic phase was washed with brine, dried with magnesium sulfate and concentrated. The residue was suspended in cold diethyl ether (50 mL) and the precipitate was collected by filtration and dried to yield N1-(4-bromophenyl)-2-fluorobenzamide (9.6 g, 0.0326 mol) as a white solid.

Workup

  1. concentrationconcentrated
  2. customthe residue partitioned between ethyl acetate (120 mL) and water (100 mL)
  3. washThe organic phase was washed with brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated
  6. filtrationthe precipitate was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-c41e225e29f24ffebab5bd7cae9dcf1f
Source dataset
uspto-grants-2008_02
Patent number
US07332497B2

Reaction notes

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