Sodium t-butoxide → HCID 59375006, compound

HRID 661818Notes

Reaction equation

HRID 661818 reaction equation
[Br:1][C:2]1[C:3]([CH3:20])=[C:4]([NH:8][C:9](=[O:19])[C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[CH2:17]Br)[CH:5]=[CH:6][CH:7]=1.CC(C)([O-])C.[Na+]>C1COCC1.O>[Br:1][C:2]1[C:3]([CH3:20])=[C:4]([N:8]2[CH2:17][C:11]3[C:10](=[CH:15][C:14]([F:16])=[CH:13][CH:12]=3)[C:9]2=[O:19])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 23676156Sodium t-butoxideHCID 66605334HCID 66605334, compound

Product 1

HCID 59375006HCID 59375006, compoundYield 58.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Step 3 A mixture of N-(3-bromo-2-methylphenyl)-2-(bromomethyl)-5-fluorobenzamide (2.54 g, 6.33 mmol) and sodium tert-butoxide (0.913 g, 9.50 mmol) in THF (80 mL) was stirred at rt for 30 min. The mixture was diluted with water and extracted with twice with DCM. The combined organic phases were washed with water, dried and concentrated. The residue was purified by column chromatography (eluting with hexane-EtOAc) to provide 2-(3-bromo-2-methylphenyl)-6-fluoroisoindolin-1-one as a white solid (1.18 g, 58%). 1H NMR (400 MHz, chloroform-d) δ 7.59-7.65 (2H, m), 7.45-7.50 (1H, m), 7.33 (1H, td, J=8.6, 2.5 Hz), 7.19-7.24 (1H, m), 7.15 (1H, t, J=7.9 Hz), 4.68 (2H, s), 2.31 (3H, s). Mass spectrum m/z 320, 322 (M+H)+.

Workup

  1. extractionextracted with 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 hexane-EtOAc)

Sources & evidence

ORD record
ord-d4c8b37550e74b8d82ff2a18b8cdec6e
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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