Phosphorus oxide (P4O10) → 2-(3-Bromo-phenyl)-1-(5-phenyl-furan-2-yl)-ethanone
Reaction equation
[C:1]1([C:7]2[O:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:12][C:13]1[CH:14]=[C:15]([CH2:19][C:20](O)=[O:21])[CH:16]=[CH:17][CH:18]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>ClC1C=CC=CC=1Cl>[Br:12][C:13]1[CH:14]=[C:15]([CH2:19][C:20]([C:9]2[O:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:11][CH:10]=2)=[O:21])[CH:16]=[CH:17][CH:18]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
2-Phenyl-furan (119)(50 mg, 0.28 mmol) and (3-bromo-phenyl)-acetic acid (134 mg, 0.63 mmol) were dissolved in ortho-dichlorobenzene (4 ml). P2O5 (202 mg, 1.42 mmol) was added as a suspension in ortho-dichlorobenzene (2 ml). The reaction mixture was heated to 80° C. for 2 h and cooled to room temperature overnight. After the addition of further P2O5 (202 mg, 1.42 mmol), heating was resumed at 90° C. for 3 h. The reaction mixture was cooled to 0° C. and quenched with H2O (15 ml). The organic layer was separated and the aqueous layer was washed with DCM (3×10 ml). The combined organic layers were dried (MgSO4), filtered and the DCM removed in vacuo. The ortho-dichlorobenzene solution was loaded to a silica-gel column and flushed with heptane (100 ml). The title compound was then eluted with 10% EtOAc in heptane.
Workup
- temperaturecooled to room temperature overnight
- temperatureheating
- temperatureThe reaction mixture was cooled to 0° C.
- customquenched with H2O (15 ml)
- customThe organic layer was separated
- washthe aqueous layer was washed with DCM (3×10 ml)
- dry with materialThe combined organic layers were dried (MgSO4)
- filtrationfiltered
- customthe DCM removed in vacuo
- customflushed with heptane (100 ml)
- washThe title compound was then eluted with 10% EtOAc in heptane
Sources & evidence
- ORD record
- ord-d90d1e2c213944cc8e3794232f98a127
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07326732B2
Reaction notes
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