Triethylamine → 3-Methanesulfonyl-5-trifluoromethyl-benzoic acid methyl ester

HRID 878114Notes

Reaction equation

HRID 878114 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:3]=1.CCN(CC)CC.[C]=O.C[CH2:26][O:27][C:28](C)=[O:29]>CO.ClCCl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:26][O:27][C:28](=[O:29])[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 532169861-Bromo-3-(methylsulfonyl)-5-(trifluoromethyl)benzeneHCID 178418416HCID 178418416, compound

Product 1

HCID 706632513-Methanesulfonyl-5-trifluoromethyl-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 887MethanolSolvent

Procedure

The mixture consisting of 1-bromo-3-(methylsulfonyl)-5-(trifluoromethyl)benzene (0.20 g, 0.66 mmol, Combi-Blocks, Inc.), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (20.4 mg, 0.025 mmol, CAS RN 72287-26-4) and NEt3 (0.134 g, 0.184 mL, 1.32 mmol) in EtOAc (2 mL) and methanol (2 mL) was stirred at 110° C. under a 70 bar carbon monoxide atmosphere for 20 h. After cooling to room temperature silica gel was added and the brown suspension evaporated. The compound was purified by silica gel chromatography on a 20 g column using a MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 50:50). Light brown oil (0.156 g; 83%). MS (GC_MS (EI)): m/z=282.0 [M].

Workup

  1. additionwas added
  2. customthe brown suspension evaporated
  3. customThe compound was purified by silica gel chromatography on a 20 g column
  4. washeluting with a gradient of n-heptane:EtOAc (100:0 to 50:50)

Sources & evidence

ORD record
ord-f30eefa387f94de288ec9fbc5aa2b259
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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