Phosphorus oxychloride → 3-Bromo-4-chloro-7-methylthieno[3,2-c]pyridine

Reaction equation

[Br:1][C:2]1[C:6]2[C:7](=O)[NH:8][CH:9]=[C:10]([CH3:11])[C:5]=2[S:4][CH:3]=1.O=P(Cl)(Cl)[Cl:15]>>[Br:1][C:2]1[C:6]2[C:7]([Cl:15])=[N:8][CH:9]=[C:10]([CH3:11])[C:5]=2[S:4][CH:3]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 184507923-Bromo-7-methylthieno[3,2-c]pyridin-4(5h)-one

Product 1

HCID 184507713-Bromo-4-chloro-7-methylthieno[3,2-c]pyridineYield 64%

Procedure

A solution of Example 277B (10.25 g, 42.1 mmol) in POCl3 (50 mL) was stirred at reflux for 2 hours, cooled to room temperature, diluted with ice water, and stirred vigorously resulting in a precipitate which was collected by filtration. The filter cake was further purified by silica gel chromatography on silica gel with dichloromethane to provide 7.14 g (64% yield) of the desired product. MS (ESI(+)) m/e 261.9, 263.9 (M+H)+.

Workup

temperatureat reflux for 2 hours
customresulting in a precipitate which
filtrationwas collected by filtration
customThe filter cake was further purified by silica gel chromatography on silica gel with dichloromethane

Sources & evidence

ORD record: ord-dd9e246723684765a7f6c158b264892d
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273736B2

Reaction notes

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