Dimethylformamide → Tert-butyl 3-chloro-2,4-difluorobenzoate

HRID 240585Notes

Reaction equation

HRID 240585 reaction equation
C([O:5][CH:6]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])N(C)C)(C)(C)C.[Cl:15][C:16]1[C:17]([F:26])=[C:18]([CH:22]=[CH:23][C:24]=1[F:25])C(O)=O.CN(C=O)C>C([O-])(O)=O.[Na+].CCOC(C)=O>[Cl:15][C:16]1[C:24]([F:25])=[C:23]([CH:22]=[CH:18][C:17]=1[F:26])[C:6]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:5]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamineHCID 27735323-Chloro-2,4-difluorobenzoic acid

Product 1

HCID 58046346Tert-butyl 3-chloro-2,4-difluorobenzoate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
80 °C

Procedure

A 125 mL, single-neck, round-bottomed flask was charged with di-tert-butoxy-N,N-dimethylmethanamine (48.2 ml, 201 mmol), 3-chloro-2,4-difluorobenzoic acid (9.67 g, 50.2 mmol), and DMF (50 ml). The reaction was heated to 80° C. for 48 hours. After cooling to ambient temperature, the reaction was diluted with saturated NaHCO3 and EtOAc. The aqueous phase was extracted with EtOAc, and the combined organic phases were washed with saturated NaHCO3 and brine, dried, filtered and concentrated to provide the desired product as a gold oil.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionThe aqueous phase was extracted with EtOAc
  3. washthe combined organic phases were washed with saturated NaHCO3 and brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fa4412622b96455780588c4a1f85a6ca
Source dataset
uspto-grants-2014_02
Patent number
US08648087B2

Reaction notes

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