Methane → HCID 66733704, compound

HRID 1929618Notes

Reaction equation

HRID 1929618 reaction equation
[CH2:1]([O:5][C:6](=[O:20])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[C:11]([Cl:19])[CH:10]=1)[CH2:2][CH2:3][CH3:4].C>[Br-].[Zn+2].[Br-].[Pd].CC(=O)OCC>[CH2:1]([O:5][C:6](=[O:20])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:17])([F:18])[F:16])=[C:11]([Cl:19])[CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 2

HCID 297MethaneHCID 66734074HCID 66734074, compound

Product 1

HCID 66733704HCID 66733704, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 10421208Zinc bromideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(3-chloro-4-trifluoromethyl-phenyl)-acrylic acid butyl ester (7.030 g; 22.921 mmol), zinc bromide (1.031 g; 4.584 mmol), and 10% palladium over activated charcoal (0.403 g) was placed under nitrogen before EA (150 ml) was added. The resulting suspension was placed under vacuum, then under hydrogen (1 atm), and the reaction mixture was vigorously stirred at rt for 9 h. The reaction mixture was filtered over a pad of celite, and concentrated under reduced pressure to give the expected product 3-(3-chloro-4-trifluoromethyl-phenyl)-propionic acid butyl ester as a yellow oil which was further dried under HV (8.430 g; 100%). LC-MS: tR=1.16 min.; [M+H]+: no ionisation.

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered over a pad of celite
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a3209521dff647caae7f4efa6e42d196
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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