Ethyl Acrylate → HCID 131732999, compound

HRID 2177241Notes

Reaction equation

HRID 2177241 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([OH:9])=[C:4]([F:10])[CH:3]=1.[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[CH:12]=[CH2:13].CCN(C(C)C)C(C)C>Cl[Pd]Cl.CN(C)C=O>[F:10][C:4]1[CH:3]=[C:2](/[CH:13]=[CH:12]\[C:11]([O:15][CH2:16][CH3:17])=[O:14])[CH:7]=[C:6]([F:8])[C:5]=1[OH:9]

Participants

6

Reactant 3

HCID 8821Ethyl AcrylateHCID 81531DiisopropylethylamineHCID 27362924-Bromo-2,6-difluorophenol

Product 1

HCID 131732999HCID 131732999, compound

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Into a 250-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 4-bromo-2,6-difluorophenol (6.3 g, 30.15 mmol, 1.00 equiv), ethyl prop-2-enoate (17.2 g, 171.80 mmol, 5.70 equiv), P(toly)3 (18.24 g), DIEA (11.6 g, 89.76 mmol, 2.98 equiv), PdCl2 (0.531 g), N,N-dimethylformamide (100 mL). The resulting solution was stirred overnight at 80° C. The reaction was then quenched by the addition of 30 mL water. The resulting solution was extracted with 3×50 mL of ethyl acetate and the organic layers combined and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (30/70). The collected fractions were combined and concentrated under vacuum. This resulted in 6 g (79%) of ethyl (2Z)-3-(3,5-difluoro-4-hydroxyphenyl)prop-2-enoate as yellow oil. Mass spectrum (ESI, m/z): Calcd. for C11H10F2O3, 229.1 (M+H). found 229.1

Workup

  1. customInto a 250-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. customThe reaction was then quenched by the addition of 30 mL water
  4. extractionThe resulting solution was extracted with 3×50 mL of ethyl acetate
  5. concentrationconcentrated under vacuum
  6. concentrationconcentrated under vacuum
  7. customThis resulted in 6 g (79%) of ethyl (2Z)-3-(3,5-difluoro-4-hydroxyphenyl)prop-2-enoate as yellow oil

Sources & evidence

ORD record
ord-1101ab8841c3497186bdae44d54ca5a0
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

Loading…