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

HRID 2387039Notes

Reaction equation

HRID 2387039 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 vacuo and the residue partitioned between ethyl acetate (100 ml) and 1N HCl (100 ml). The organics were separated and dried over magnesium sulfate, filtered and solvent removed in vacuo 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 vacuo
  2. customthe residue partitioned between ethyl acetate (100 ml) and 1N HCl (100 ml)
  3. customThe organics were separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customsolvent removed in vacuo

Sources & evidence

ORD record
ord-74bc447110a84bd9ba1cc0382a754085
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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