Water → (5-Bromo-3-methylthiophen-2-yl)(4-propylphenyl)methanone

HRID 1469198Notes

Reaction equation

[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][CH:10]=1)=[O:8].[Br-:18].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.O>C(O)(=O)C>[Br:18][C:5]1[S:4][C:3]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][CH:10]=2)=[O:8])=[C:2]([CH3:1])[CH:6]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (3-methylthiophen-2-yl)(4-propylphenyl)methanone (44, 1.12 g, 4.58 mmol) in acetic acid (4.67 mL) was added pyridinium tribromide (3.67 g, 11.5 mmol). The reaction mixture was heated to 50° C. for 3 hours. After cooling to room temperature, the mixture was poured into water (50 mL) and extracted with EtOAc (100 mL). The organic phase was dried over MgSO4 and evaporated under vacuum. The residue was further purified by silica column chromatography (Biotage) to provide (5-bromo-3-methylthiophen-2-yl)(4-propylphenyl)methanone (45, 0.95 g, 2.95 mmol, 64%).

Workup

temperatureAfter cooling to room temperature
extractionextracted with EtOAc (100 mL)
dry with materialThe organic phase was dried over MgSO4
customevaporated under vacuum
customThe residue was further purified by silica column chromatography (Biotage)

Sources & evidence

ORD record: ord-555aa7f58a6e4defb8dc4616d2e8bb12
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006187B2

Reaction notes

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