Dimethyl Sulfoxide → HCID 89544754, compound

HRID 2283389Notes

Reaction equation

HRID 2283389 reaction equation
Br[CH2:2][C:3]1[C:4]([F:18])=[C:5]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])[C:6]([Cl:9])=[CH:7][CH:8]=1.C(=O)(O)[O-:20].[Na+].CS(C)=O>C(OCC)(=O)C>[C:10]([C:5]1[C:4]([F:18])=[C:3]([CH:8]=[CH:7][C:6]=1[Cl:9])[CH:2]=[O:20])(=[O:11])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 516892Sodium BicarbonateHCID 89544688HCID 89544688, compound

Product 1

HCID 89544754HCID 89544754, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Step 3 A mixture of (3-bromomethyl-6-chloro-2-fluoro-phenyl)-phenyl-methanone (292 mg, 0.896 mmol), sodium bicarbonate (700 mg, 8.33 mmol) and dimethylsulfoxide (10 ml) was heated to 80 degC for 3 hours. The reaction mixture was then allowed to cool, ethyl acetate was added, and the mixture was washed with water, aqueous lithium chloride and brine before drying (MgSO4) and concentrating in vacuo. The residue was purified by silica chromatography eluting with 0-20% ethyl acetate/petroleum ether to furnish 3-benzoyl-4-chloro-2-fluoro-benzaldehyde (115 mg oil, 90% clean). 1H NMR (400 MHz, CDCl3): 10.34 (1H, s), 7.97 (1H, dd), 7.91-7.86 (2H, m), 7.72-7.67 (1H, m), 7.55 (2H, t), 7.44 (1H, d), 7.28 (1H, s). MS: [M+NH4]+ 280

Workup

  1. temperaturewas heated to 80 degC for 3 hours
  2. temperatureto cool
  3. washthe mixture was washed with water, aqueous lithium chloride and brine
  4. dry with materialbefore drying (MgSO4)
  5. concentrationconcentrating in vacuo
  6. customThe residue was purified by silica chromatography
  7. washeluting with 0-20% ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-4eb91cc340e64dcc933917224e2eece9
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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