Methyl iodide → HCID 23295998, compound

HRID 1954285Notes

Reaction equation

HRID 1954285 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8](=[O:16])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[CH:5]=[C:4]([CH2:17][CH3:18])[C:3]=1[OH:19].[C:20]([O-])([O-])=O.[K+].[K+].IC>>[Br:1][C:2]1[CH:7]=[C:6]([C:8](=[O:16])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[CH:5]=[C:4]([CH2:17][CH3:18])[C:3]=1[O:19][CH3:20]

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 23296012HCID 23296012, compound

Product 1

HCID 23295998HCID 23295998, compoundYield 66%

Procedure

At ambient temperature, to a stirred mixture containing 2-bromo-4-(2-chlorobenzoyl)-6-ethylphenol (14.56 g, 42.82 mmol) and K2CO3 (8.90 g, 64.5 mmol) in N,N-DMF (11.6 mL) was added iodomethane (3.98 mL, 64.4 mmol). After 48 h, the reaction was quenched with H2O (300 mL) and extracted with hexane. The organic extracts were washed with H2O (2×100 mL), brine (1×100 mL), dried (Na2SO4) and concentrated. Purification on Biotage KP-Sil eluting with a 0, 2.5 & 5% EtOAc/hexane step gradient gave 10.0 g (66%) of the title compound. 1H NMR: consistent. mass spectrum (EI) m/z 352 (M+). Anal. Calcd. for C16H14BrClO2.0.2H2O: C, 53.79; H, 4.06; N, 0.00. Found: C, 53.89; H, 3.91; N, 0.08.

Workup

  1. customthe reaction was quenched with H2O (300 mL)
  2. extractionextracted with hexane
  3. washThe organic extracts were washed with H2O (2×100 mL), brine (1×100 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification on Biotage KP-Sil
  7. washeluting with a 0, 2.5 & 5% EtOAc/hexane step gradient

Sources & evidence

ORD record
ord-274257dca60247aab7083d815cffed3f
Source dataset
uspto-grants-2000_09
Patent number
US06121271

Reaction notes

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