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

HRID 661821Notes

Reaction equation

HRID 661821 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 (1H, dd, J=7.9, 1.1 Hz), 7.46 (1H, d, J=2.4 Hz), 7.42 (1H, d, J=8.4 Hz), 7.15-7.26 (3H, m), 4.67 (2H, s), 3.92 (3H, s), 2.34 (3H, 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-14136ee23a414be8b6a8cc30efe32b6c
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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