Boron tribromide → HCID 59375155, compound

HRID 661897Notes

Reaction equation

HRID 661897 reaction equation
[Br:1][C:2]1[C:3]([CH3:20])=[C:4]([N:8]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:17]C)[CH:14]=3)[C:9]2=[O:19])[CH:5]=[CH:6][CH:7]=1.B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[C:3]([CH3:20])=[C:4]([N:8]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([OH:17])[CH:14]=3)[C:9]2=[O:19])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 66606533HCID 66606533, compound2×

Product 1

HCID 59375155HCID 59375155, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-(3-bromo-2-methylphenyl)-5-methoxyisoindolin-1-one (Intermediate 1-4, 100 mg, 0.30 mmol) and 1.0 M boron tribromide in DCM (900 μL, 0.90 mmol) was stirred at rt for 4 h. The reaction mixture was diluted with DCM, washed with NaHCO3 (aq) and dried and concentrated. The residue was purified by column chromatography (eluting with EtOAc-hexane) to provide 2-(3-bromo-2-methylphenyl)-5-hydroxyisoindolin-1-one as an off-white solid (62 mg, 65%). 1H NMR (400 MHz, chloroform-d) δ 10.27 (1H, br. s.), 7.64 (1H, dd, J=7.9, 0.9 Hz), 7.59 (1H, d, J=8.4 Hz), 7.44 (1H, d, J=7.3 Hz), 7.25 (1H, t, J=7.9 Hz), 6.98 (1H, d, J=1.5 Hz), 6.93 (1H, dd, J=8.3, 2.1 Hz), 4.77 (2H, s), 2.20 (3H, s). Mass spectrum m/z 318, 320 (M+H)+.

Workup

  1. washwashed with NaHCO3 (aq)
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (eluting with EtOAc-hexane)

Sources & evidence

ORD record
ord-f0f518b8c6f04ac297190da79cf50648
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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