Sodium t-butoxide → HCID 59375006, compound

HRID 2361447Notes

Reaction equation

HRID 2361447 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

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 room temperature for 30 min. The mixture was diluted with water and extracted with twice with CH2Cl2. The combined organic phases were washed with water, dried and concentrated. The residue was purified by column chromatography on silica gel, eluting with EtOAc-hexane to provide the desired product as a white solid (1.18 g, 58% yield). LCMS (M+H)+ m/z 320, 322.

Workup

  1. extractionextracted with twice with CH2Cl2
  2. washThe combined organic phases were washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel
  6. washeluting with EtOAc-hexane

Sources & evidence

ORD record
ord-4ebaa2558ac94aeea8c4aa400c9b2256
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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