Methyl Acrylate → Methyl 3-(3-(benzyloxy)-5-fluorophenyl)acrylate

HRID 709681Notes

Reaction equation

HRID 709681 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[C:11](Br)[CH:10]=1)[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].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:19]=[CH:18][C:17]([O:21][CH3:22])=[O:20])[CH:12]=[C:13]([F:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 112545161-(Benzyloxy)-3-bromo-5-fluorobenzene

Product 1

HCID 131733901Methyl 3-(3-(benzyloxy)-5-fluorophenyl)acrylate

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-(benzyloxy)-3-bromo-5-fluorobenzene (6.60 g) in acetonitrile (130 mL) were added methyl acrylate (13.7 g), triphenylphosphine (3.36 g) and triethylamine (14.5 g), and toluene (2.0 mL) and palladium acetate (480 mg) were further added. The reaction mixture was stirred at 100° C. for 96 hr, and the solvent was evaporated under reduced pressure.

Workup

  1. additionwere further added
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-62617ea181ec4e649af81bb8498b222d
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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