Dichloromethane → HCID 86602645, compound

HRID 2100597Notes

Reaction equation

HRID 2100597 reaction equation
Br[C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:13]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:16])[CH:14]=[CH2:15].C(N(CC)CC)C.ClCCl>CN(C=O)C.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:18]([O:17][C:13](=[O:16])/[CH:14]=[CH:15]/[C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 75617Benzyl acrylateHCID 80186Ethyl 2-bromobenzoate

Product 1

HCID 86602645HCID 86602645, compoundYield 92.8%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of ethyl 2-bromobenzoate (1.15 g, 5.0 mmol) in 20 mL of DMF was added benzyl acrylate (1.22 g, 7.5 mmol) and triethylamine (1.39 mL, 10.0 mmol). The mixture was degassed and then there was added [1,1′-bis(diphenylphoshino)ferrocene]dichloropalladium (II), complex with dichloromethane (12.2 mg, 0.015 mol). The reaction mixture was stirred at 90° C. for 18 h. The reaction mixture was allowed to cool and was diluted with EtOAc. The organics were washed with water and brine, dried (MgSO4) and concentrated to an oil. The residue was purified (ISCO, elution with 0-15% EtOAc/hexane) to give 1.44 g (92%) of the title compound. 1H NMR (CDCl3): δ 8.51 (d, 1H), 7.96 (d, 1H), 7.57 (d, 1H), 7.50 (t, 1H), 7.45-7.22 (overlapping m, 6H), 6.35 (d, 1H), 5.26 (s, 2H), 4.38 (q, 2H), 1.37 (t, 3H). LRMS (ESI): 311.2 (M+H)+.

Workup

  1. customThe mixture was degassed
  2. temperatureto cool
  3. washThe organics were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated to an oil
  6. customThe residue was purified
  7. wash(ISCO, elution with 0-15% EtOAc/hexane)

Sources & evidence

ORD record
ord-d8c6f152024a49a69cfcd8313777390c
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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