Methyl Acrylate → (E)-3-(4-benzyloxy-3-fluoro-phenyl)-acrylic acid methyl ester

HRID 62842

Reaction equation

HRID 62842 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[CH:11][C:10]=1[F:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O:21][CH3:22])(=[O:20])[CH:18]=[CH2:19].F[B-](F)(F)F.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH3:22][O:21][C:17](=[O:20])/[CH:18]=[CH:19]/[C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([F:16])[CH:11]=1

Participants

6

Reactant 3

HCID 7294Methyl AcrylateHCID 187574911-(Benzyloxy)-4-bromo-2-fluorobenzeneHCID 44558591Tri-t-butylphosphine fluoroborate

Product 1

HCID 90118296(E)-3-(4-benzyloxy-3-fluoro-phenyl)-acrylic acid methyl esterYield 22%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

1-Benzyloxy-4-bromo-2-fluoro-benzene (1.62 g, 5.7 mmol) obtained in Step A was added with methyl acrylate (1 mL), 1,4-dioxane (19 mL), Pd2(dba)3(0.1 g, 0.11 mmol), TEA (1.6 mL, 11.4 mmol) and tri-t-butylphosphine tetrafluoroborate (0.16 g, 0.57 mmol), and the mixture was stirred at 100° C. for 6 hours. The reactant was filtered by using celite, and the filtrate was washed with EtOAc and purified by column chromatography to obtain the title compound (0.37 g, 22%).

Workup

  1. filtrationThe reactant was filtered
  2. washthe filtrate was washed with EtOAc
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-2b392dbbc5af4db7ac645857e703b8bf
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Linked notes

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