Ethyl bromodifluoroacetate → HCID 53375273, compound

HRID 2405157Notes

Reaction equation

HRID 2405157 reaction equation
I[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH2:13]([O:15][C:16](=[O:21])[C:17](Br)([F:19])[F:18])[CH3:14]>[Cu].CS(C)=O>[CH2:9]([O:8][C:6](=[O:7])[C:5]1[CH:11]=[CH:12][C:2]([C:17]([F:19])([F:18])[C:16]([O:15][CH2:13][CH3:14])=[O:21])=[CH:3][CH:4]=1)[CH3:10]

Participants

5

Reactant 2

HCID 69585Ethyl bromodifluoroacetateHCID 142891Ethyl 4-iodobenzoate2×

Product 1

HCID 53375273HCID 53375273, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
55 °C

Procedure

According to the Kumadaki method (supra) and the above-described scheme, ethyl 4-iodobenzoate (Compound 1d; 1.38 g, 5.0 mmol), bromodifluoroacetic acid ethyl ester (1.015 g, 5.0 mmol), copper powder (635.5 mg, 10.0 mmol) and DMSO (10 mL) were put into a two-neck reaction tube, and the mixture was stirred under argon atmosphere at 55° C. for 24 hours. The reaction mixture was extracted with ethyl acetate and washed with water, and an organic layer was dried with anhydrous sodium sulfate. Ethyl acetate was distilled away under reduced pressure, and by carrying out purification by silica gel column chromatography, 4-(2-ethoxy-1,1-difluoro-2-oxethyl)benzoic acid ethyl ester (Compound 2d) was obtained with a yield of 80%.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialan organic layer was dried with anhydrous sodium sulfate
  4. distillationEthyl acetate was distilled away under reduced pressure
  5. custompurification by silica gel column chromatography

Sources & evidence

ORD record
ord-3e0e5c8a570c459a8bd73a11b58cdd5a
Source dataset
uspto-grants-2014_08
Patent number
US08802886B2

Reaction notes

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