Sodium t-butoxide → HCID 59375006, compound

HRID 1811000Notes

Reaction equation

HRID 1811000 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 (2 H, m), 7.45-7.50 (1 H, m), 7.33 (1 H, td, J=8.6, 2.5 Hz), 7.19-7.24 (1 H, m), 7.15 (1 H, t, J=7.9 Hz), 4.68 (2 H, s), 2.31 (3 H, 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-505241807ef94ac5a1f6870fa05fed8f
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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