Methanol → 6-Hydroxy-2,3-dihydro-1H-isoindol-1-one

HRID 1761023Notes

Reaction equation

HRID 1761023 reaction equation
C[O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][NH:8][C:9]2=[O:12])=[CH:5][CH:4]=1.B(Br)(Br)Br.CO>C(Cl)Cl>[OH:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][NH:8][C:9]2=[O:12])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 140056236-Methoxy-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 115283646-Hydroxy-2,3-dihydro-1H-isoindol-1-oneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-methoxy-2,3-dihydro-isoindol-1-one (167 mg, 1.0 mmol) and boron tribromide (1 M in CH2Cl2, 3.6 mL, 3.6 mmol) in CH2Cl2 (8 mL) at −78° C. was stirred for 18 h at RT. The mixture was then cooled to −78° C. and MeOH (20 mL) was added. After 2 h at −78° C. the mixture was evaporated and the residue purified by chromatography (SiO2, CH2Cl2:2N NH3-MeOH 9:1) to afford the title product (147 mg, 100%) as a white solid. MS m/e=148.0 (M−H+).

Workup

  1. temperatureThe mixture was then cooled to −78° C.
  2. customAfter 2 h at −78° C. the mixture was evaporated
  3. customthe residue purified by chromatography (SiO2, CH2Cl2:2N NH3-MeOH 9:1)

Sources & evidence

ORD record
ord-530ca7994aa4463cb7b34054dda6e966
Source dataset
uspto-grants-2005_01
Patent number
US06846832B2

Reaction notes

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