Thionyl Chloride → 5-Bromothiophene-2-carbonyl chloride

HRID 581085Notes

Reaction equation

HRID 581085 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.S(Cl)([Cl:12])=O>>[Br:1][C:2]1[S:6][C:5]([C:7]([Cl:12])=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 3491155-Bromothiophene-2-carboxylic acid

Product 1

HCID 6057125-Bromothiophene-2-carbonyl chloride

Procedure

Following the procedure of Example 32, 2.07 g (10.0 mmoles) of commercially available 5-bromo-2-thiophenecarboxylic acid was reacted with 10 ml of thionyl chloride to give 2.35 g of crude 5-bromo-2-thiophenecarbonyl chloride as a red oil. The total crude acid chloride was coupled to 1.76 g (8.33 mmoles) of 5-chloro-2-oxindole-1-carboxamide by the procedure in Example 32 using 3.05 g (25.0 mmoles) of 4-(N,N-dimethylamino)pyridine and 50 ml of N,N-dimethylformamide. Acidic workup gave a solid which was recrystallized to give 1.77 g (4.43 mmoles, 53% yield) of title compound as reddish-brown crystals, m.p. 228-229° C. (tetrahydrofuran).

Sources & evidence

ORD record
ord-6bebad824a4c422da1ac5a334ca4d9b5
Source dataset
uspto-grants-1999_07
Patent number
US05919809

Reaction notes

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