Ethyl Acrylate → Ethyl (2E)-3-[4-hydroxy-2-(trifluoromethyl)phenyl]prop-2-enoate

HRID 2177312Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].[C:13]([O:17][CH2:18][CH3:19])(=[O:16])[CH:14]=[CH2:15].CCN(C(C)C)C(C)C>Cl[Pd]Cl.CN(C)C=O>[OH:8][C:5]1[CH:6]=[CH:7][C:2](/[CH:15]=[CH:14]/[C:13]([O:17][CH2:18][CH3:19])=[O:16])=[C:3]([C:9]([F:12])([F:11])[F:10])[CH:4]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Into a 500-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 4-bromo-3-(trifluoromethyl)phenol (5 g, 20.75 mmol, 1.00 equiv), N,N-dimethylformamide (60 mL), ethyl prop-2-enoate (10.5 g, 104.88 mmol, 5.06 equiv), PdCl2 (370 mg, 2.09 mmol, 0.10 equiv), P(tolyl)3 (1.28 g, 4.21 mmol, 0.20 equiv), DIEA (16.25 g). The resulting solution was stirred for overnight at 90° C. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/8). This resulted in 2.6 g (42%) of ethyl (2E)-3-[4-hydroxy-2-(trifluoromethyl)phenyl]prop-2-enoate as a light yellow solid.

Workup

customInto a 500-mL round-bottom flask purged
temperaturemaintained with an inert atmosphere of nitrogen
concentrationThe resulting mixture was concentrated under vacuum
customThis resulted in 2.6 g (42%) of ethyl (2E)-3-[4-hydroxy-2-(trifluoromethyl)phenyl]prop-2-enoate as a light yellow solid

Sources & evidence

ORD record: ord-40226ac7e7a3447c9b9553d7579d2e6e
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067898B1

Reaction notes

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