Acetone → 2-(Benzyloxy)-1-chloro-3-fluorobenzene

HRID 39015Notes

Reaction equation

HRID 39015 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[OH:9].C([O-])([O-])=O.[K+].[K+].[CH3:16][C:17]([CH3:19])=O>>[CH2:16]([O:9][C:3]1[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[C:17]1[CH:19]=[CH:4][CH:3]=[CH:2][CH:7]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 27737102-Chloro-6-fluorophenol

Product 1

HCID 532169822-(Benzyloxy)-1-chloro-3-fluorobenzene

Conditions

Temperature
65 °C

Procedure

A mixture of 2-chloro-6-fluorophenol (25 g, 170 mmol), acetone (200 ml), K2CO3 (47.08 g, 340 mmol) and bensylbromide (22.31 ml, 187 mmol) was heated at 65° C. for 16 h. The solution was filtered and evaporated. Water (100 ml) was added, and the solution was extracted with EtOAc. The combined organic phases were dried (Na2SO4) and evaporated to dryness to give the title compound (32.3 g). MS m/z (rel. intensity, 70 eV) 236 (M+, 2), 117 (4), 92 (8), 91 (bp), 65 (13).

Workup

  1. filtrationThe solution was filtered
  2. customevaporated
  3. additionWater (100 ml) was added
  4. extractionthe solution was extracted with EtOAc
  5. dry with materialThe combined organic phases were dried (Na2SO4)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-38288b2fe72543d2874ba82dd88f7891
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

Loading…