Water → N-(2-bromo-3-fluorophenyl)butyramide

HRID 1964290Notes

Reaction equation

HRID 1964290 reaction equation
[Br:1][C:2]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:10](Cl)(=[O:14])[CH2:11][CH2:12][CH3:13].N1C=CC=CC=1.O>C(Cl)Cl>[Br:1][C:2]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:10](=[O:14])[CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 8855Butyryl chlorideHCID 147700052-Bromo-3-fluoroaniline

Product 1

HCID 59129259N-(2-bromo-3-fluorophenyl)butyramideYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromo-3-fluoroaniline (2.0 g, 11 mmol) in CH2Cl2 (50 mL) was added butyryl chloride (1.3 g, 13 mmol) and pyridine (1.7 g, 21 mmol) at 0° C. The mixture was stirred at room temperature for 24 h. Water (20 mL) was added and the mixture was extracted with CH2Cl2 (50 mL×3). The organic layers were dried anhydrous over Na2SO4 and evaporated under vacuum to give N-(2-bromo-3-fluorophenyl)butyramide (2.0 g, 73%), which was directly used in the next step.

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (50 mL×3)
  2. customevaporated under vacuum

Sources & evidence

ORD record
ord-74d36b3df94c40d2a64db695489951df
Source dataset
uspto-grants-2013_04
Patent number
US08415387B2

Reaction notes

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