Benzyl Alcohol → 2-Fluoro-6-(phenylmethoxy)benzamide

HRID 896196Notes

Reaction equation

HRID 896196 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[F:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17](F)[C:13]=1[C:14]([NH2:16])=[O:15].Cl>CN(C=O)C>[CH2:1]([O:8][C:17]1[CH:18]=[CH:19][CH:20]=[C:12]([F:11])[C:13]=1[C:14]([NH2:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 874392,6-Difluorobenzamide

Product 1

HCID 152191982-Fluoro-6-(phenylmethoxy)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl alcohol (24 ml, 0.229 mol) is added portionwise to a suspension of sodium hydride (9.16 g, 0.229 mol) in DMF (300 ml) and stirred at room temperature for 1 h. 2,6-Difluorobenzamide (30 g, 0.190 mol) is added in one portion and stirring is continued overnight at room temperature. The reaction mixture is poured into 1N HCl (1.5 l) and extracted with dichloromethane. The extract is washed with water and saline, dried (MgSO4), and evaporated to give product as a white solid suitable for use in the next step (39.6 g, 85%); MS for C14H12FNO2 m/z 246 (M+H)+.

Workup

  1. stirringstirring
  2. waitis continued overnight at room temperature
  3. extractionextracted with dichloromethane
  4. washThe extract is washed with water and saline
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give product as a white solid suitable for use in the next step (39.6 g, 85%)

Sources & evidence

ORD record
ord-84a7333aba6b4376b02cb0e9c1e311b1
Source dataset
uspto-grants-2005_07
Patent number
US06919329B2

Reaction notes

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