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

HRID 908889Notes

Reaction equation

HRID 908889 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-9d828ca4fbd949d3b9f207f6229b1d95
Source dataset
uspto-grants-2011_09
Patent number
US08017643B2

Reaction notes

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