Sulfuryl chloride → Ethyl 2-chloro-2-(2-fluorobenzoyl)acetate

HRID 2227460Notes

Reaction equation

HRID 2227460 reaction equation
S(Cl)([Cl:4])(=O)=O.[F:6][C:7]1[CH:20]=[CH:19][CH:18]=[CH:17][C:8]=1[C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:10]>C(Cl)Cl>[Cl:4][CH:11]([C:9](=[O:10])[C:8]1[CH:17]=[CH:18][CH:19]=[CH:20][C:7]=1[F:6])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 296342Ethyl 3-(2-fluorophenyl)-3-oxopropanoate

Product 1

HCID 18473854Ethyl 2-chloro-2-(2-fluorobenzoyl)acetateYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sulfuryl chloride (4.25 g, 32 mmol) was added dropwise to a solution ethyl 2-(2-flurobenzoyl)acetate (6.30 g, 30 mmol) in CH2Cl2 (75 mL) at room temperature. No exotherm was observed after 30 minutes, only slight bubbling. After stirring overnight TLC analysis indicated that all of the starting material had been consumed. The reaction mixture was treated with H2O (100 mL). The resultant mixture was stirred for 20 minutes and the phases were separated. The organic phase was washed with H2O (2×100 mL), dried over anhydrous MgSO4, filtered and concentrated in vacuo to give 6.85 g (93% yield) of the desired product as an orange oil: 1H NMR (CDCl3) δ8.0-7.9 (m, 1H), 7.6-7.5 (m, 1H), 7.3-7.1 (m, 2H), 5.6 (s, 1H), 4.25 (q, 2H), 1.25 (t, 3H).

Workup

  1. customhad been consumed
  2. additionThe reaction mixture was treated with H2O (100 mL)
  3. stirringThe resultant mixture was stirred for 20 minutes
  4. customthe phases were separated
  5. washThe organic phase was washed with H2O (2×100 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-450b0bccb1a84b929e3d5780fb2226fb
Source dataset
uspto-grants-2002_07
Patent number
US06413997B1

Reaction notes

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