Hexane → 2-Bromo-1-(2-phenoxypyrimidin-5-yl)methanone

HRID 2274492Notes

Reaction equation

[O:1]([C:8]1[N:13]=[CH:12][C:11]([C:14](=[O:16])C)=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br-:17].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.CCCCCC>ClCCl>[Br:17][C:8]1([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:13]=[CH:12][C:11]([CH:14]=[O:16])=[CH:10][NH:9]1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution consisting of 1-(2-phenoxypyrimidin-5-yl)ethanone (Step B, 400 mg, 1.87 mmol) in dichloromethane (14 mL) was added tetrabutylammonium tribromide (990 mg, 2.05 mmol). The reaction mixture was sealed with a screw top and warmed at 40° C. overnight and allowed to cool to room temperature. Hexane (4 mL) was subsequently added. After three hours and little precipitation, additional (150 mg) tetrabutylammonium tribromide was added and the reaction mixture was stirred overnight at room temperature. The pale yellow precipitate that formed was collected on a filter and washed with 1:1 dichloromethane-hexane to afford the title intermediate (375 mg, 68%); Rf 0.43 with 3:1 v/v hexanes-ethyl acetate; MS (ESI+) m/z 295, 293 (M+1, Br isotopes).

Workup

customThe reaction mixture was sealed with a screw top
temperatureto cool to room temperature
customlittle precipitation, additional (150 mg) tetrabutylammonium tribromide
additionwas added
customThe pale yellow precipitate that formed
customwas collected on
filtrationa filter
washwashed with 1:1 dichloromethane-hexane

Sources & evidence

ORD record: ord-f5fcb93393f24e76ac5f731bef4530a1
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126973B2

Reaction notes

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