1-(2-Phenylpyrimidin-5-yl)ethanone → 2-Bromo-1-(2-phenylpyrimidin-5-yl)ethanone

HRID 42288

Reaction equation

[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br-:16].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl>[Br:16][CH2:14][C:13]([C:10]1[CH:9]=[N:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:12][CH:11]=1)=[O:15]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution consisting of 1-(2-phenylpyrimidin-5-yl)ethanone (Step A, 700 mg, 3.5 mmol) in dichloromethane (25 mL) was added tetrabutylammonium tribromide (1.87 g, 3.90 mmol). The reaction mixture was sealed with a screw top and warmed at 40° C. for 5 hours and allowed to cool to room temperature over a weekend. The pale yellow precipitate formed was collected on a filter and washed with 1:1 dichloromethane-hexane to afford the title intermediate (770 mg, 79%); Rf 0.31 with 9:1 v/v hexanes-ethyl acetate; MS (ESI+) m/z 279, 277 (M+1, Br isotopes).

Workup

customThe reaction mixture was sealed with a screw top
temperatureto cool to room temperature over a weekend
customThe pale yellow precipitate formed
customwas collected on
filtrationa filter
washwashed with 1:1 dichloromethane-hexane

Sources & evidence

ORD record: ord-49ef573663a4412a8513614681ec736e
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536185B2

Linked notes

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