1,3-Difluorobenzene → Methyl 2,4-difluoro-alpha-oxobenZeneacetate

HRID 1994213Notes

Reaction equation

HRID 1994213 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].[Cl-].[C:14]([O:19][CH3:20])(=[O:18])[C:15]([O-])=[O:16]>C(=S)=S>[F:1][C:2]1[CH:3]=[C:4]([F:8])[CH:5]=[CH:6][C:7]=1[C:15](=[O:16])[C:14]([O:19][CH3:20])=[O:18]

Participants

5

Reactant 3

HCID 97411,3-DifluorobenzeneHCID 6451240Aluminum(III) ChlorideHCID 22574234Monomethyl oxalate chloride

Product 1

HCID 22574245Methyl 2,4-difluoro-alpha-oxobenZeneacetate

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Conditions

Temperature
20 °C

Procedure

50 g (0.44 mol) of 1,3-difluorobenzene is dissolved at 20° C. in 135 ml of carbon disulfide with 73.5 g (0.55 mol) AlCl3 and then 55.15 g (0.45 mol) of methyl oxalate chloride is added and the mixture is stirred for 2.5 hours at 20° C. Ice-cold 2 N aqueous hydrochloric acid is added dropwise while cooling, extracted with ethyl acetate; the organic phase is washed with water and 10% aqueous Na2CO3 solution, dried over MgSO4, and evaporated to dryness. Yield: 38.0 g (43% of theory).

Workup

  1. temperaturewhile cooling
  2. extractionextracted with ethyl acetate
  3. washthe organic phase is washed with water and 10% aqueous Na2CO3 solution
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-0c6c8c21b7fd4fc8ab3c7d8c976cdf99
Source dataset
uspto-grants-2010_01
Patent number
US07652138B2

Reaction notes

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