Sulfuryl chloride → 2-Chloro-4-(trifluoromethoxy)phenol

HRID 229349Notes

Reaction equation

HRID 229349 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.S(Cl)([Cl:16])(=O)=O>>[Cl:16][C:6]1[CH:5]=[C:4]([O:3][C:2]([F:11])([F:12])[F:1])[CH:9]=[CH:8][C:7]=1[OH:10]

Participants

3

Reactant 2

HCID 24648Sulfuryl chlorideHCID 70015p-(Trifluoromethoxy)phenol

Product 1

HCID 130447832-Chloro-4-(trifluoromethoxy)phenolYield 94.1%

Procedure

A solution of 4-trifluoromethoxyphenol (20 g, 0.11 mole) and sulfuryl chloride (18.20 mL, 0.22 mole) was stirred at room temperature for five hours. The excess of sulfuryl chloride was evaporated by rotary evaporator. The residue was dissolved in 50 mL of dichloromethane and washed with 50 mL of H2O. The organic layer was separated, dried over MgSO4, filtered and concentrated to yield 22 g of the product. The crude product was purified over a silica gel column using 10% ethyl acetate in hexane to yield 16.4 g of the product. 1H-NMR (DMSO, 500-MHz), δ 10.59 (s, 1H), 7.43 (d, J=2.75 Hz, 1H), 7.18 (dd, J1=2.75 Hz, J2=7.16 Hz, 1H), 7.03 (d, J=7.16 Hz, 1H). MS (electro-spray) [M−H] 211.4.

Workup

  1. customThe excess of sulfuryl chloride was evaporated by rotary evaporator
  2. dissolutionThe residue was dissolved in 50 mL of dichloromethane
  3. washwashed with 50 mL of H2O
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8a4f09244e734935af7613d203f22a95
Source dataset
uspto-grants-2009_07
Patent number
US07563792B2

Reaction notes

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