4-Bromobutyronitrile → 3-bromo-4-chloro-N-[2-(3-cyano-propoxy)-phenyl]-N-methyl-benzamide

HRID 1848620Notes

Reaction equation

HRID 1848620 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]#[N:6].[Br:7][C:8]1[CH:9]=[C:10]([CH:22]=[CH:23][C:24]=1[Cl:25])[C:11]([N:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[OH:21])[CH3:14])=[O:12]>CN(C=O)C>[Br:7][C:8]1[CH:9]=[C:10]([CH:22]=[CH:23][C:24]=1[Cl:25])[C:11]([N:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH2:2][CH2:3][CH2:4][C:5]#[N:6])[CH3:14])=[O:12]

Participants

4

Reactant 2

HCID 214124-BromobutyronitrileHCID 686031173-bromo-4-chloro-N-(2-hydroxy-phenyl)-N-methyl-benzamide

Product 1

HCID 686031543-bromo-4-chloro-N-[2-(3-cyano-propoxy)-phenyl]-N-methyl-benzamideYield 92.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

CsCO3 (5.17 g, 15.87 mmol) was added to a solution of 4-bromo-butyronitrile (0.63 mL, 6.35 mmol) and 3-bromo-4-chloro-N-(2-hydroxy-phenyl)-N-methyl-benzamide (1.80 g, 5.29 mmol, Step 3B) in DMF (20 mL). The mixture was stirred at room temperature for approximately 16 hrs and was partitioned between ethyl acetate and water. The ethyl acetate layer was separated, washed with water and brine, and was dried over MgSO4. The organic filtrate was evaporated to yield 3-bromo-4-chloro-N-[2-(3-cyano-propoxy)-phenyl]-N-methyl-benzamide as a light yellow solid (2.0 g). MS [M+H]+: 408.9; tR=2.39 min. (method 1)

Workup

  1. customwas partitioned between ethyl acetate and water
  2. customThe ethyl acetate layer was separated
  3. washwashed with water and brine
  4. dry with materialwas dried over MgSO4
  5. customThe organic filtrate was evaporated

Sources & evidence

ORD record
ord-f1cba4d924d34b16ac4e15c0f091f803
Source dataset
uspto-grants-2015_02
Patent number
US08952161B2

Reaction notes

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