Pyridine → 2-(1-Chloro-2,2,2-trifluoroethyl)phenol

HRID 858679Notes

Reaction equation

HRID 858679 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]([F:17])([F:16])[CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])O.N1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:3][CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])[C:6]([F:17])([F:16])[F:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 28292952-(2,2,2-Trifluoro-1-hydroxyethyl)phenol

Product 1

HCID 587627412-(1-Chloro-2,2,2-trifluoroethyl)phenol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thionyl chloride (2.28 ml) was added to a solution of 2-(2,2,2-trifluoro-1-hydroxyethyl)phenol (3.0 g) and pyridine (1.23 ml) in toluene (50 ml). The reaction was stirred at room temperature for 1 hr, after which time the toluene was removed in vacuuo and the residue partitioned between ethyl acetate (100 ml) and 1 HCl (100 ml). The organics were separated and dried over magnesium sulfate, filtered and solvent removed in vacuuo to afford the title compound as a clear oil (3.0 g). 1H NMR (CDCl3): δ 5.93 (m, 1H), 6.90 (d, J=4.52 Hz, 1H), 7.10 (m, 1H), 7.35 (m, 1H), 7.69 (m, 1H).

Workup

  1. customafter which time the toluene was removed in vacuuo
  2. customthe residue partitioned between ethyl acetate (100 ml) and 1 HCl (100 ml)
  3. customThe organics were separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customsolvent removed in vacuuo

Sources & evidence

ORD record
ord-bc7df068716a47ea96a1331318e9f7ac
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

Loading…