Benzyl Bromide → HCID 19888144, compound

HRID 654046Notes

Reaction equation

HRID 654046 reaction equation
[F:1][C:2]([F:24])([F:23])[CH2:3][NH:4][C:5](=[O:22])[C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]([NH:13][C:14](=[O:20])[CH2:15][O:16][C:17](=[O:19])[CH3:18])[C:7]=1[OH:21].C[O-].[Na+].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1COCC1>[F:24][C:2]([F:1])([F:23])[CH2:3][NH:4][C:5](=[O:22])[C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]([NH:13][C:14](=[O:20])[CH2:15][O:16][C:17](=[O:19])[CH3:18])[C:7]=1[O:21][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10942334Sodium MethoxideHCID 19888147HCID 19888147, compound

Product 1

HCID 19888144HCID 19888144, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7.75 g (22 mmol) of 3-acetoxyacetamido-5-fluoro-2-hydroxy-benzoic acid-(2,2,2,-trifluoro-ethyl)amide (Example 37d) is dissolved in 50 ml of dry THF. 1.35 g (25 mmol) of sodium methylate is added, stirred for 15 minutes at room temperature, 4.27 g (25 mmol) of benzylbromide is added and refluxed for 1 hour. The reaction solution is then cooled to room temperature, NaBr is filtered off, the filtrate is concentrated by evaporation in a vacuum and the residue is chromatographed on silica gel 60 with ethyl acetate/hexane. 5.2 g=53.4% of the theoretical yield is obtained as an amorphous solid.

Workup

  1. temperaturerefluxed for 1 hour
  2. temperatureThe reaction solution is then cooled to room temperature
  3. filtrationNaBr is filtered off
  4. concentrationthe filtrate is concentrated by evaporation in a vacuum
  5. customthe residue is chromatographed on silica gel 60 with ethyl acetate/hexane
  6. custom5.2 g=53.4% of the theoretical yield
  7. customis obtained as an amorphous solid

Sources & evidence

ORD record
ord-b2fe06abb6db420eacc96d5f3a035ea3
Source dataset
uspto-grants-1992_07
Patent number
US05130119

Reaction notes

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