Dimethylformamide → 5-Fluorothiophene-2-carbonyl chloride

HRID 1638221Notes

Reaction equation

HRID 1638221 reaction equation
[F:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.S(Cl)([Cl:12])=O.CN(C=O)C>C(Cl)Cl>[F:1][C:2]1[S:6][C:5]([C:7]([Cl:12])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 118049015-fluorothiophene-2-carboxylic acid

Product 1

HCID 186966265-Fluorothiophene-2-carbonyl chlorideYield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of the title compound of Example 2 (200 mg, 1.37 mmol), thionyl chloride (500 μl, 6.85 mmol) and DMF (20 μl) in dry methylene chloride was refluxed for 2 hours. The solvents were evaporated and the residue dried in vacuo to give 183 mg (81%) of the title product as a brown solid, mp 123-5 C. 1H-NMR (CDCl3): δ 7.74 (m, 1H), 6.64 (m, 1H),). GC-MS (m/e, %) 166/164 (M+, 11), 129(100).

Workup

  1. temperaturewas refluxed for 2 hours
  2. customThe solvents were evaporated
  3. customthe residue dried in vacuo

Sources & evidence

ORD record
ord-6606681330704b27b9792a102bdf3fb9
Source dataset
uspto-grants-2000_03
Patent number
US06043379

Reaction notes

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