Methane → HCID 66733743, compound

HRID 1929617Notes

Reaction equation

HRID 1929617 reaction equation
[CH2:1]([O:5][C:6](=[O:18])[CH:7]=[CH:8][C:9]1[CH:14]=[C:13]([F:15])[C:12]([Cl:16])=[C:11]([F:17])[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:18])[CH2:7][CH2:8][C:9]1[CH:14]=[C:13]([F:15])[C:12]([Cl:16])=[C:11]([F:17])[CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 2

HCID 297MethaneHCID 66734199HCID 66734199, compound

Product 1

HCID 66733743HCID 66733743, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 10421208Zinc bromideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(4-chloro-3,5-difluoro-phenyl)-acrylic acid butyl ester (5.000 g; 18.202 mmol), zinc bromide (0.819 g; 3.640 mmol), and 10% palladium over activated charcoal (0.320 g) was placed under nitrogen before EA (140 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 22 h. The reaction mixture was filtered over a pad of celite, and concentrated under reduced pressure to give the expected product 3-(4-chloro-3,5-difluoro-phenyl)-propionic acid butyl ester as a slightly yellow oil which was further dried under HV (5.020 g; 98%). LC-MS: tR=1.14 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-6ccca8724b494eb79d2f2758af0b9250
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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