tert-Butyl acrylate → HCID 131736321, compound

HRID 1054131Notes

Reaction equation

HRID 1054131 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([F:11])[F:10].[C:12]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[CH:13]=[CH2:14]>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([CH:9]([F:11])[F:10])=[C:2](/[CH:14]=[CH:13]/[C:12]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:7]=1

Participants

5

Reactant 2

HCID 15458tert-Butyl acrylateHCID 667449422-Bromo-4-chloro-1-(difluoromethyl)benzene

Product 1

HCID 131736321HCID 131736321, compoundYield 22.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of Intermediate 14A (0.88 g, 3.64 mmol) in DMF (10 mL) was added tert-butyl acrylate (1.401 g, 10.93 mmol), TEA (1.270 mL, 9.11 mmol) and Pd(OAc)2 (0.082 g, 0.364 mmol). The reaction was warmed to 90° C. After 5 h, the reaction was cooled to rt and then filtered to remove the solid. The filtrate was diluted with EtOAc, washed with 1M HCl, saturated NaHCO3, and brine. The organic phase was dried over MgSO4, filtered and concentrated. Purification by normal phase chromatography gave Intermediate 14B (232 mg, 22% yield) as a tan oil. MS (ESI) m/z: 233.1 (M-tBu)+.

Workup

  1. temperaturethe reaction was cooled to rt
  2. filtrationfiltered
  3. customto remove the solid
  4. additionThe filtrate was diluted with EtOAc
  5. washwashed with 1M HCl, saturated NaHCO3, and brine
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by normal phase chromatography

Sources & evidence

ORD record
ord-3acab4bd2b3b46d9938ce3b25ad3edac
Source dataset
uspto-grants-2016_07
Patent number
US09394276B2

Reaction notes

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