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

HRID 1991332Notes

Reaction equation

HRID 1991332 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-306e84422e7a4885b1bf3256e1bca76d
Source dataset
uspto-grants-2010_01
Patent number
US07645781B2

Reaction notes

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