Allyl bromide → HCID 86714061, compound

HRID 576355Notes

Reaction equation

HRID 576355 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH2:7](Br)[CH:8]=[CH2:9].[CH2:11]([C:14]1[C:15]([Cl:24])=[C:16]([CH:19]=[C:20]([Br:23])[C:21]=1[SH:22])[C:17]#[N:18])[CH:12]=[CH2:13]>CC#N>[CH2:11]([C:14]1[C:15]([Cl:24])=[C:16]([CH:19]=[C:20]([Br:23])[C:21]=1[S:22][CH2:9][CH:8]=[CH2:7])[C:17]#[N:18])[CH:12]=[CH2:13]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 86714062HCID 86714062, compound

Product 1

HCID 86714061HCID 86714061, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a mixture of crude 3-allyl-5-bromo-2-chloro-4-mercaptobenzonitrile and K2CO3 (1.79 g, 12.9 mmol) in CH3CN (80 mL), allylbromide (1.12 mL, 12.9 mmol) was added dropwise. The reaction mixture was stirred overnight at room temperature, and then filtered off. The resulting solution was evaporated and purified by silica gel chromatography to give the desired product 94 (1.1 g, 77.7% overall yield) as a white solid.

Workup

  1. additionwas added dropwise
  2. filtrationfiltered off
  3. customThe resulting solution was evaporated
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-3f039f92f70b43839b8a46a05969e17c
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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