t-Butyl bromide → Tert-butyl 4-cyano-5-(methylthio)thiophene-2-carboxylate

HRID 506441Notes

Reaction equation

HRID 506441 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:10]([OH:12])=[O:11])[S:6][C:7]=1[S:8][CH3:9])#[N:2].[C:13](Br)([CH3:16])([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.CC(N(C)C)=O>[C:1]([C:3]1[CH:4]=[C:5]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[S:6][C:7]=1[S:8][CH3:9])#[N:2]

Participants

6

Reactant 3

HCID 10485t-Butyl bromideHCID 11430Potassium CarbonateHCID 455943124-Cyano-5-methylsulfanylthiophene-2-carboxylic acid

Product 1

HCID 66785900Tert-butyl 4-cyano-5-(methylthio)thiophene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-cyano-5-(methylthio)thiophene-2-carboxylic acid (2.0 g, 10 mmol), benzyltrimethylammonium chloride (2.25 g, 10 mmol), tertbutyl bromide (54 mL, 480 mmol), and anhydrous potassium carbonate (36 g, 260 mmol) in dimethylacetamide (100 mL) was stirred at 60° C. for 6 hours.

Sources & evidence

ORD record
ord-5dd7fee267694adf9b68347113b18d45
Source dataset
uspto-grants-2010_08
Patent number
US07786048B2

Reaction notes

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