Chloroform → Methyl 2-benzoyl-4-fluorobenzoate

HRID 469550Notes

Reaction equation

HRID 469550 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10].C(Cl)(Cl)Cl.C(N(CC)CC)C.CN(C=O)C.C[CH2:34][O:35][C:36](C)=[O:37]>CO>[C:9]([C:3]1[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=1[C:36]([O:35][CH3:34])=[O:37])(=[O:10])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 5

HCID 6212ChloroformHCID 6228DimethylformamideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 242877(2-Bromo-5-fluorophenyl)(phenyl)methanone

Product 1

HCID 67161783Methyl 2-benzoyl-4-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the product of example 35B (0.516 g, 1.85 mmol), PdCl2dppf.CHCl3 (75 mg, 0.091 mmol), and triethylamine (0.39 mL, 2.8 mmol) was stirred in 1:1 DMF:MeOH (6 mL, pre-saturated with CO) under CO (1 atm) at 80° C. for 4 hours, diluted with EtOAc, washed with water and brine, dried (Na2SO4), and filtered. The residue was chromatographed on SiO2 (3-12% Et2O/hexanes) to give 112.0 mg of the title compound as a clear gum. 1H NMR (300 MHz, DMSO) δ 8.09 (dd, 1H), 7.62-7.69 (m, 3H), 7.49-7.57 (m, 3H), 7.45 (dd, 1H), 3.57 (s, 3H).

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customThe residue was chromatographed on SiO2 (3-12% Et2O/hexanes)

Sources & evidence

ORD record
ord-09e94635ea5d44f2959ae5e12c448a81
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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