Azobisisobutyronitrile → HCID 67138806, compound

HRID 1591993Notes

Reaction equation

HRID 1591993 reaction equation
[CH3:1][Si:2]([CH3:15])([CH3:14])[CH2:3][CH2:4][O:5][C:6]([C:8]1[S:9][C:10]([CH3:13])=[CH:11][CH:12]=1)=[O:7].[Br:16]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl.[Hg]>[CH3:1][Si:2]([CH3:14])([CH3:15])[CH2:3][CH2:4][O:5][C:6]([C:8]1[S:9][C:10]([CH2:13][Br:16])=[CH:11][CH:12]=1)=[O:7]

Participants

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimide2×HCID 671384295-Methyl-thiophene-2-carboxylic acid 2-trimethylsilanylethyl ester

Product 1

HCID 67138806HCID 67138806, compound

Reagents, catalysts & solvents 2

HCID 23931MercuryCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of the title A compound, 5-methyl-thiophene-2-carboxylic acid 2-trimethylsilanyl-ethyl ester (34.15 g, 141 mmol) in CCl4 (200 mL) is treated with N-bromosuccinimide (NBS, 25.08 g, 141 mmol) and 2,2′-azobisisobutyronitrile (1.0 g, 6 mmol). The mixture is irradiated with a 450 W mercury lamp for 3 h. An additional 2.5 g of NBS is added and the mixture is further irradiated for 2 h. The mixture is filtered through Celite and a plug of silica gel. The solvent is evaporated to give 5-bromomethyl-thiophene-2-carboxylic acid 2-trimethylsilanyl-ethyl ester as a yellow liquid.

Workup

  1. customthe mixture is further irradiated for 2 h
  2. filtrationThe mixture is filtered through Celite
  3. customThe solvent is evaporated

Sources & evidence

ORD record
ord-5a721372e7a4485aab64850f49bc6764
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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