Thionyl Chloride → HCID 19876905, compound

HRID 1886076Notes

Reaction equation

HRID 1886076 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[C:10]([CH2:14]O)[CH:11]=[CH:12][CH:13]=1.S(Cl)([Cl:25])=O>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[C:10]([CH2:14][Cl:25])[CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 24386Thionyl Chloride2×HCID 19876899HCID 19876899, compound

Product 1

HCID 19876905HCID 19876905, compound

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) flask containing [(2-fluorophenyl)(3-fluorophenyl)phenyl]carbinol (20 g, 67.5 mmol) (obtained in example 1) was slowly added thionyl chloride (12.82 g, 108 mmol) with vigorous stirring. Once the reaction had been initiated (gas evolution), the rest of the thionyl chloride was added at once and the reaction mixture heated to reflux for 4 h. Volatiles were removed in vacuo and the remaining traces of thionyl chloride were removed by azeotropic evaporation with toluene (2×). The resulting residue was dissolved in petroleum ether and precipitated by cooling to -20° C. The solid was filtered and dried to afford the title compound as a slightly cream-colored solid (18.1 g, 85%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 h
  3. customVolatiles were removed in vacuo
  4. customthe remaining traces of thionyl chloride were removed by azeotropic evaporation with toluene (2×)
  5. dissolutionThe resulting residue was dissolved in petroleum ether
  6. customprecipitated
  7. temperatureby cooling to -20° C
  8. filtrationThe solid was filtered
  9. customdried

Sources & evidence

ORD record
ord-3aeaf5bdc3e440c2a7a728b3c6e72576
Source dataset
uspto-grants-1992_09
Patent number
US05149707

Reaction notes

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