Dimethylformamide → HCID 14403833, compound

HRID 1194135Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[CH:10]=[CH:11][C:12]([OH:14])=O.CN(C)C=O.S(Cl)([Cl:22])=O>>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1/[CH:10]=[CH:11]/[C:12]([Cl:22])=[O:14]

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 24386Thionyl Chloride

HCID 54286105HCID 54286105, compound

Product 1

HCID 14403833HCID 14403833, compoundYield 99%

Procedure

A solution of 5.07 g (19.9 mmol) of 3-(2-bromo-4,6-dimethylphenyl)-2-propenoic acid in 50 mL of thionyl chloride containing 50 μl of dimethylformamide (DMF) was stirred under nitrogen at room temperature for 20 hours. The volatiles were removed under reduced pressure to give 5.40 g (99%) of (E)-3-(2-bromo-4,6-dimethylphenyl)-2-propenoyl chloride as a dark brown solid: IR (film) 2960, 2920, 1750, 1620 and 1605 cm-1 ; NMR (CDCl3) δ 2.32 (3H, s), 2.40 (3H, s), 6.44 (1H, d, J=16 Hz).

Workup

customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record: ord-382dc269fe9349be9ea7101075008abb
Source dataset: uspto-grants-1989_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04812583

Reaction notes

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