4-Bromoaniline → HCID 531936, compound

HRID 897996Notes

Reaction equation

HRID 897996 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-c8f252f6b30549d48358b52d06d2deaa
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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