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Methyl Acrylate → Methyl (E)-3-(3,5-dichlorophenyl)acrylate

HRID 1480420
Notes
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Reaction equation

HRID 1480420 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[C:4]([Cl:9])[CH:3]=1.[C:10]([O:14][CH3:15])(=[O:13])[CH:11]=[CH2:12].C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6](/[CH:12]=[CH:11]/[C:10]([O:14][CH3:15])=[O:13])[CH:5]=[C:4]([Cl:9])[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 764241,3-Dichloro-5-iodobenzene

Product 1

HCID 69907122Methyl (E)-3-(3,5-dichlorophenyl)acrylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl Acetate
Solvent

Conditions

Temperature
80 °C

Procedure

To 1,3-dichloro-5-iodobenzene (300 mg, 1.099 mmol) and methyl acrylate (0.099 ml, 1.099 mmol) in DMF (10 ml) under nitrogen was added [Pd(t-BuP)]2 (56.1 mg, 0.110 mmol) and triethylamine (0.306 ml, 2.199 mmol). The reaction mixture was heated to 80° C. for 2 h. The reaction mixture was diluted with EtOAc and filtered through a silica cartridge (2 g). The organic solution was washed with water, saturated sodium bicarbonate solution, water and brine. The organic portion was dried using a phase separating column and the solvent was removed under reduced pressure to afford the title compound;

Workup

  1. filtrationfiltered through a silica cartridge (2 g)
  2. washThe organic solution was washed with water, saturated sodium bicarbonate solution, water and brine
  3. customThe organic portion was dried
  4. customseparating column
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c4cd2e1bef2c4beeb6d60d95b85fd10c
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09409895B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes