Oxalyl chloride → 2-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoyl chloride

HRID 340421Notes

Reaction equation

HRID 340421 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([C:13]([CH3:18])([CH3:17])[C:14](O)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(Cl)(=O)C([Cl:24])=O>ClCCl.CN(C=O)C>[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([C:13]([CH3:18])([CH3:17])[C:14]([Cl:24])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 98359482-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoic acid

Product 1

HCID 112671412-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

15.0 g (50 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionic acid were dissolved in 127.5 ml dichloromethane in the presence of 0.75 ml DMF. 8.76 ml (2 eq.) Oxalyl chloride were added and after 4.5 hours, the solution was rotary evaporated to dryness. 9 ml Toluene were added and the resulting solution was again rotary evaporated, then dried under high vacuum yielding 16.25 g (quant.) of 2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl chloride as a yellow oil of 86% purity according to HPLC analysis. NMR (250 MHz, CDCl3): 7.86 (br s, 1H); 7.77, (br s, 2H, 3 Harom); 1.77 (s, 6H, 2 CH3).

Workup

  1. customthe solution was rotary evaporated to dryness
  2. addition9 ml Toluene were added
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-8e12a5e265634ecc80ce34c836f51976
Source dataset
uspto-grants-2014_11
Patent number
US08895586B2

Reaction notes

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