Methanol → 5-Hydroxy-2,3-dihydro-1H-isoindol-1-one

HRID 1761007Notes

Reaction equation

HRID 1761007 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH2:6]2.B(Br)(Br)Br.CO>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH2:6]2

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 220647195-methoxy-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 225942075-Hydroxy-2,3-dihydro-1H-isoindol-1-oneYield 72.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-methoxy-2,3-dihydro-isoindol-1-one (3.7 g, 23 mmol) and boron tri-bromide (1 M in CH2Cl2, 15.2 mL, 88 mmol) in CH2Cl2 (30 mL) at −78° C. was stirred for 16 h at RT. The mixture was then cooled to −78° C. and MeOH (25 mL) was added. After 1 h at −78° C. the mixture was evaporated and the residue purified by chromatography (SiO2, CH2Cl2:2N NH3-MeOH 98:2 to 90:10) to afford the title product (2.5 g, 72%) as an off-white solid. MS m/e=148.0 (M−H+).

Workup

  1. temperatureThe mixture was then cooled to −78° C.
  2. customAfter 1 h at −78° C. the mixture was evaporated
  3. customthe residue purified by chromatography (SiO2, CH2Cl2:2N NH3-MeOH 98:2 to 90:10)

Sources & evidence

ORD record
ord-6ad00901f5cd41ffb1cb0907f550d19f
Source dataset
uspto-grants-2005_01
Patent number
US06846832B2

Reaction notes

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