m-Chloroperbenzoic acid → 2-[3,5-Bis(trifluoromethyl)phenyl]oxirane

HRID 990093Notes

Reaction equation

HRID 990093 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH:6]=[CH2:7].ClC1C=CC=C(C(OO)=[O:25])C=1>ClCCl.O>[F:1][C:2]([F:15])([F:16])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH:6]1[O:25][CH2:7]1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 27732423,5-Bis(trifluoromethyl)styrene

Product 1

HCID 139032682-[3,5-Bis(trifluoromethyl)phenyl]oxirane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3,5-bis(trifluoromethyl)styrene (13.3 g) and m-chloroperbenzoic acid (21 g) in dichloromethane (100 ml) was stirred at room temperature for 16 hours. The resulting suspension was diluted with water (100 ml) and dichloromethane (100 ml), and the organic phase was washed further with water (2×100 ml) and saturated brine (100 ml). After drying (MgSO4) the solvent was removed in vacuo and the residue purified by chromatography on silica (eluting with isohexane followed by 10% ethyl acetate in isohexane) to provide the title compound. 1H NMR (400 MHz, CDCl3) δ 2.79 (1H, dd J 6.0 Hz and 2.7 Hz), 3.23 (1H, dd J 5.9 Hz and 4.5 Hz), 3.99 (1H, dd J 4,4 Hz and 2.7 Hz), 7,74 (2H,s), 7.82 (1H, s).

Workup

  1. washthe organic phase was washed further with water (2×100 ml) and saturated brine (100 ml)
  2. dry with materialAfter drying (MgSO4) the solvent
  3. customwas removed in vacuo
  4. customthe residue purified by chromatography on silica (eluting with isohexane followed by 10% ethyl acetate in isohexane)

Sources & evidence

ORD record
ord-5127c5a4de624cc4bfe987b264a450c8
Source dataset
uspto-grants-2002_10
Patent number
US06458830B1

Reaction notes

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