Water → HCID 86680182, compound

HRID 1184927Notes

Reaction equation

HRID 1184927 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([NH:11][C:12](=[O:24])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([C:22]#[N:23])([CH3:21])[CH3:20])[CH:14]=2)[CH:7]=[CH:8][C:9]=1[CH3:10])(=[O:3])[CH3:2].[Br:25]Br.O>O1CCOCC1.C(Cl)Cl>[Br:25][CH2:2][C:1]([C:4]1[CH:5]=[C:6]([NH:11][C:12](=[O:24])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([C:22]#[N:23])([CH3:21])[CH3:20])[CH:14]=2)[CH:7]=[CH:8][C:9]=1[CH3:10])=[O:3]

Participants

6

Reactant 3

HCID 962WaterHCID 24408BromineHCID 67125611HCID 67125611, compound

Product 1

HCID 86680182HCID 86680182, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-(3-acetyl-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamide 112 (1.136 mmol, 364 mg) in dioxane (4 mL) and CH2Cl2 (1 mL) at 0° C. was added BROMINE (1.250 mmol, 0.064 mL). The reaction was stirred overnight at room temperature. Water was added and extracted with CH2Cl2. Organic layer was dried and evaporated to give N-(3-(2-bromoacetyl)-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamide 113 (450 mg, 99%). (m/z)=401 (M+H)+.

Workup

  1. extractionextracted with CH2Cl2
  2. customOrganic layer was dried
  3. customevaporated

Sources & evidence

ORD record
ord-9281d0ea1fc941fa99c3f4da58759f44
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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