Triethylamine → ethyl (2E)-3-(4-chloro-2-nitrophenyl)prop-2-enoate

HRID 910868Notes

Reaction equation

HRID 910868 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C(N(CC)CC)C.[C:19]([O:23][CH2:24][CH3:25])(=[O:22])[CH:20]=[CH2:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH2:24]([O:23][C:19](=[O:22])/[CH:20]=[CH:21]/[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10])[CH3:25]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 11776TriphenylphosphineHCID 27949042-Bromo-5-chloronitrobenzene

Product 1

HCID 10912128ethyl (2E)-3-(4-chloro-2-nitrophenyl)prop-2-enoate

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

1-bromo-4-chloro-2-nitrobenzene (5 g), triethylamine (4.42 ml), ethyl acrylate (22.9 ml), palladium (II) acetate (0.048 g) and triphenylphosphine (0.111 g) in DMF (30 ml) was refluxed at 87° C. for 10 h. Toluene was added and the mixture washed with 2M hydrochloric acid and water. The organics were dried and concentrated under reduced pressure to a brown oil which was triturated with isohexane to give a light brown solid. Yield 4.95 g.

Workup

  1. washthe mixture washed with 2M hydrochloric acid and water
  2. customThe organics were dried
  3. concentrationconcentrated under reduced pressure to a brown oil which
  4. customwas triturated with isohexane
  5. customto give a light brown solid

Sources & evidence

ORD record
ord-1adb7d286a674f418c430af5480d2cec
Source dataset
uspto-grants-2011_09
Patent number
US08022248B2

Reaction notes

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