Potassium Carbonate → HCID 2779414, compound

HRID 2066615Notes

Reaction equation

HRID 2066615 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.C([O-])([O-])=O.[K+].[K+].Br[CH2:20][CH:21]1[CH2:23][O:22]1>CC(C)=O>[F:1][C:2]([F:11])([F:12])[O:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:20][CH:21]2[CH2:23][O:22]2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 70015p-(Trifluoromethoxy)phenol

Product 1

HCID 2779414HCID 2779414, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
59 °C

Procedure

A mixture of 4-trifluoromethoxyphenol (0.152 mL, 1.17 mmol), K2CO3 (260 mg, 1.17 mmol) and 2-(bromomethyl)oxirane (76) (0.30 mL, 3.51 mmol) in anhydrous acetone (3 mL) was stirred in a sealed vial at 59° C. for 36 h. The resulting mixture was filtered, washing with CH2Cl2, and then the filtrate was evaporated to dryness and the residue was chromatographed on silica gel. Elution with 0-15% CH2Cl2/pentane firstly gave foreruns, and then further elution with 20-25% CH2Cl2/pentane gave 2-{[4-(trifluoromethoxy)phenoxy]methyl}oxirane (77) (similarly prepared by Cao et al., WO 2008112483A2 using epichlorohydrin) (260 mg, 95%) as an oil; 1H NMR (CDCl3) δ 7.14 (br dd, J=9.0, 0.6 Hz, 2H), 6.91 (dt, J=9.1, 3.0 Hz, 2H), 4.23 (dd, J=11.1, 3.1 Hz, 1H), 3.94 (dd, J=11.1, 5.7 Hz, 1H), 3.34 (m, 1H), 2.91 (dd, J=4.8, 4.2 Hz, 1H), 2.75 (dd, J=4.9, 2.6 Hz, 1H).

Workup

  1. filtrationThe resulting mixture was filtered
  2. washwashing with CH2Cl2
  3. customthe filtrate was evaporated to dryness
  4. customthe residue was chromatographed on silica gel
  5. washElution with 0-15% CH2Cl2/pentane firstly gave foreruns
  6. washfurther elution with 20-25% CH2Cl2/pentane

Sources & evidence

ORD record
ord-b05e1510fe4649109a8e4af7bb480c05
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

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