Acetic Acid Mixture with Hydrobromic Acid → (1S,1aR,7bS)-1-(bromomethyl)-4,7-difluoro-1a,7b-dihydrocyclopropa[c]chromene-2(1H)-one
Reaction equation
[F:1][C:2]1[C:3]([O:16]C)=[C:4]([C@@H:9]2[C@H:14]3[C@@H:10]2[CH2:11]O[C:13]3=[O:15])[C:5]([F:8])=[CH:6][CH:7]=1.[BrH:18].CC(O)=O>O>[Br:18][CH2:11][C@H:10]1[C@@H:9]2[C@H:14]1[C:13](=[O:15])[O:16][C:3]1[C:2]([F:1])=[CH:7][CH:6]=[C:5]([F:8])[C:4]=12Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
(1S,5R,6S)-6-(3,6-difluoro-2-methoxyphenyl)-3-oxabicyclo[3.1.0]hexan-2-one (130 mg, 0.55 mmol) was mixed with 1.2 ml of 30% HBr/AcOH (6 mmol) and heated in a sealed vessel at stirring for about 4 h at 90° C. The reaction mixture was then cooled down, mixed with water and extracted into diethyl ether (3×20 ml). Ether extract was washed with sat. sodium bicarbonate solution and brine. Dried over magnesium sulfate. Concentration gave 160 mg of white solid material. 98% yield.
Workup
- temperatureheated in a sealed vessel
- temperatureThe reaction mixture was then cooled down
- extractionextracted into diethyl ether (3×20 ml)
- extractionEther extract
- washwas washed with sat. sodium bicarbonate solution and brine
- dry with materialDried over magnesium sulfate
- concentrationConcentration
Sources & evidence
- ORD record
- ord-d44154570daa444d945eb3ea619a6985
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07915295B2
Reaction notes
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