Water → 2-(3-Bromo-2-methylphenyl)-6-methoxyisoindolin-1-one

HRID 1811003Notes

Reaction equation

HRID 1811003 reaction equation
[Br:1][C:2]1[C:3]([CH3:22])=[C:4]([NH:8][CH2:9][C:10]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:11]=2[C:12](OC)=[O:13])[CH:5]=[CH:6][CH:7]=1.CC(C)([O-])C.[Na+].O>C1COCC1>[Br:1][C:2]1[C:3]([CH3:22])=[C:4]([N:8]2[CH2:9][C:10]3[C:11](=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)[C:12]2=[O:13])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23676156Sodium t-butoxideHCID 66606189Methyl 2-((3-bromo-2-methylphenylamino)methyl)-5-methoxybenzoate

Product 1

HCID 593750342-(3-Bromo-2-methylphenyl)-6-methoxyisoindolin-1-oneYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step 3 A solution of methyl 2-((3-bromo-2-methylphenylamino)methyl)-5-methoxybenzoate (360 mg, 0.988 mmol) in THF (10 mL) was treated with sodium tert-butoxide (142 mg, 1.483 mmol) and stirred at rt overnight. The mixture was treated with water and extracted twice with DCM. The combined organic phases were washed with water, dried and concentrated. The residue was purified by column chromatography (eluting with EtOAc-hexane) to provide 2-(3-bromo-2-methylphenyl)-6-methoxyisoindolin-1-one as a white solid (246 mg, 75%). 1H NMR (400 MHz, chloroform-d) δ 7.62 (1 H, dd, J=7.9, 1.1 Hz), 7.46 (1 H, d, J=2.4 Hz), 7.42 (1 H, d, J=8.4 Hz), 7.15-7.26 (3 H, m), 4.67 (2 H, s), 3.92 (3 H, s), 2.34 (3 H, s). Mass spectrum m/z 332, 334 (M+H)+.

Workup

  1. extractionextracted twice with DCM
  2. washThe combined organic phases were washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (eluting with EtOAc-hexane)

Sources & evidence

ORD record
ord-da3dbf8c450d4d1988d9fde8e7fe2bd0
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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