Methanol → 7-hydroxy-2-methyl-2,3-dihydro-1H-isoindol-1-one
Reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:15]=1[C:14](=[O:16])[N:13]([CH3:17])[CH2:12]2.CO>ClCCl>[OH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:15]=1[C:14](=[O:16])[N:13]([CH3:17])[CH2:12]2Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
100 ml of a 1 M solution of boron tribromide in dichloromethane at −78° C. were added dropwise to a solution of 3.7 g of 7-methoxy-2-methyl-2,3-dihydroisoindol-1-one in 50 ml of dichloromethane. The reaction medium was stirred at −78° C. for 1 hour and then left to return to 0° C. for 1 hour. The reaction medium was cooled to −78° C. and then slowly hydrolyzed by adding, dropwise, 20 ml of methanol (temperature below −60° C.). The reaction medium was washed with 30 ml of a 1 M sodium dihydrogen phosphate solution and the aqueous phase was extracted with ethyl acetate (2×50 ml). The organic phases were combined, dried over magnesium sulfate and evaporated. The residue was triturated with diethyl ether. 2.6 g of 7-hydroxy-2-methyl-2,3-dihydroisoindol-1-one were obtained.
Workup
- waitleft
- waitto return to 0° C. for 1 hour
- temperatureThe reaction medium was cooled to −78° C.
- additionslowly hydrolyzed by adding
- washThe reaction medium was washed with 30 ml of a 1 M sodium dihydrogen phosphate solution
- extractionthe aqueous phase was extracted with ethyl acetate (2×50 ml)
- dry with materialdried over magnesium sulfate
- customevaporated
- customThe residue was triturated with diethyl ether
Sources & evidence
- ORD record
- ord-e4f7189123084555ae7895ab2a99ae59
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09090596B2
Reaction notes
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