Benzyl Alcohol → 3-Benzyloxy-5-(Trifluoromethyl)Pyridine

HRID 2171353Notes

Reaction equation

HRID 2171353 reaction equation
Cl[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[C:12]1([CH2:18][OH:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C)C=O.O>[CH2:18]([O:19][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 244Benzyl AlcoholHCID 27366983-Chloro-5-(trifluoromethyl)pyridine

Product 1

HCID 218518253-Benzyloxy-5-(Trifluoromethyl)Pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 3-chloro-5-(trifluoromethyl)pyridine (10.0 g, 55.1 mmol) in N,N-dimethylformamide (DMF) (150 mL) was added dropwise phenylmethanol (5.96 g, 55.1 mmol) under nitrogen at rt. The reaction mixture was stirred at 40° C. for 2 h, diluted with water (300 mL) and extracted with ethyl acetate (300 mL×3). Combined organic parts were washed with brine, dried over anhydrous Na2SO4 and concentrated. The crude product (100 g) was used into next step without further purification.

Workup

  1. extractionextracted with ethyl acetate (300 mL×3)
  2. washCombined organic parts were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe crude product (100 g) was used into next step without further purification

Sources & evidence

ORD record
ord-241cedde8fd9463b8d309d113463fe99
Source dataset
uspto-grants-2015_06
Patent number
US09051325B2

Reaction notes

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