Sulfuryl chloride → 2-Chloro-1-(4-fluorophenyl)-2-phenylethan-1-one

HRID 1844775Notes

Reaction equation

HRID 1844775 reaction equation
S(Cl)([Cl:4])(=O)=O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:21])[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][CH:8]=1>C(Cl)Cl>[Cl:4][CH:14]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:13]([C:10]1[CH:9]=[CH:8][C:7]([F:6])=[CH:12][CH:11]=1)=[O:21]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 3182354'-Fluoro-2-phenylacetophenone

Product 1

HCID 234556682-Chloro-1-(4-fluorophenyl)-2-phenylethan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
12.5 °C

Procedure

Sulfuryl chloride (66.6 g, 0.493 mol) is taken in a 4 necked RB flask equipped with mechanical strring rod, pressure equalization funnel and a CaCl2 guard tube. The contents of the flask are cooled to 10-15° C. A solution of 1-(4-Fluorophenyl)-2-phenyl ethanone (100 g, 0.467 mol) in 150 ml of methylene chloride is added to the above flask in about 30-45 min while maintaining the temperature between 10-15° C. After completion of addition, the reaction mass is then stirred for additional 2½ hours at 15-20° C. TLC examination of reaction mixture showed the absence of starting material. The reaction mixture is slowly poured over crushed ice (600 g) and further dilueted with methylene chloride (200 ml). The methylene chloride layer is separated and washed twice with 5% aqueous sodium bicarbonate (200 ml) followed by 5% aqueous sodium chloride(200 ml). The methylene chloride layer is dried over sodium sulphate. Methylene chloride is removed by distillation completely to obtain 2-Chloro-1-(4-fluorophenyl)-2-phenylethanone as a pale yellow liquid.

Workup

  1. customequipped with mechanical strring rod, pressure equalization funnel and a CaCl2 guard tube
  2. temperaturewhile maintaining the temperature between 10-15° C
  3. additionAfter completion of addition
  4. customTLC examination of reaction mixture
  5. additionThe reaction mixture is slowly poured
  6. customThe methylene chloride layer is separated
  7. washwashed twice with 5% aqueous sodium bicarbonate (200 ml)
  8. dry with materialThe methylene chloride layer is dried over sodium sulphate
  9. customMethylene chloride is removed by distillation completely

Sources & evidence

ORD record
ord-c95fe3f347a2445da73e8f207f9a0e30
Source dataset
uspto-grants-2015_02
Patent number
US08946479B2

Reaction notes

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