Sodium Hydroxide → (R)-2-(4-chloro-3-fluorophenyl)oxirane

HRID 530588Notes

Reaction equation

HRID 530588 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([F:22])[CH:16]=2)[OH:14])(=O)=O)=CC=1.FC1C=CC(C(=O)C)=CC=1C(F)(F)F.[OH-].[Na+]>CCOCC>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C@@H:13]2[CH2:12][O:14]2)=[CH:16][C:17]=1[F:22]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 6056784'-Fluoro-3'-(trifluoromethyl)acetophenoneHCID 117870261(R)-2-(4-chloro-3-fluorophenyl)-2-hydroxyethyl 4-methylbenzenesulfonate

Product 1

HCID 94590788(R)-2-(4-chloro-3-fluorophenyl)oxirane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(R)-2-(4-chloro-3-fluorophenyl)-2-hydroxyethyl 4-methylbenzenesulfonate (prepared as previously described in Example 1 (steps a-b) except substituting 1-(3-chloro-4-fluorophenyl)ethanone for 1-(4-fluoro-3-(trifluoromethyl)phenyl)ethanone, 3.35 g, 9.72 mmol) was dissolved in ether (80 mL) and 2N NaOH solution (25 mL) was added. The mixture was stirred at room temperature for 6 h until all starting material was consumed. The mixture was separated and the ether layer was washed with water. The organic layer was dried with sodium sulfate and solvents were removed to afford (R)-2-(4-chloro-3-fluorophenyl)oxirane as a colorless oil which was dried in vacuum (1.66 g). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.71-2.80 (m, 1H) 3.18 (dd, J=5.31, 4.04 Hz, 1H) 3.82-3.89 (m, 1H) 7.01-7.12 (m, 2H) 7.39 (dd, J=8.46, 7.45 Hz, 1H).

Workup

  1. customwas consumed
  2. customThe mixture was separated
  3. washthe ether layer was washed with water
  4. dry with materialThe organic layer was dried with sodium sulfate and solvents
  5. customwere removed

Sources & evidence

ORD record
ord-226c60bdf29f44469e0c0d048a6b01b2
Source dataset
uspto-grants-2016_05
Patent number
US09353096B2

Reaction notes

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