Bromomethyl 4-methoxyphenyl ketone → HCID 12330847, compound

HRID 2298116Notes

Reaction equation

HRID 2298116 reaction equation
[C:1]([O-])(=[S:3])[CH3:2].[K+].Br[CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)=[O:9]>C(O)C>[C:1]([CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)=[O:9])(=[S:3])[CH3:2]

Participants

4

Reactant 2

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 23670855Potassium ethanethioate

Product 1

HCID 12330847HCID 12330847, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Potassium thioacetate (2.28 g, 20 mmol) was added to a solution of 2-bromo-4′-methoxy acetophenone (4.58 g, 20 mmol) in absolute ethanol (150 ml). The reaction was stirred at ambient temperature under nitrogen for 16 hours at which time the white precipitate that had formed was filtered and the ethanol removed at reduced pressure. The residue was dissolved in dichloromethane (250 ml) and washed with water (200 ml), brine (200 ml), dried over Na2SO4 and the solvent removed at reduced pressure. The resulting residue was chromatographed on silica with a gradient from 10%-35% ethyl acetate in hexane to yield 3.4 g (76%) of 2-thioacetyl-4′-methoxy acetophenone. 1H NMR (CDCl3) δ 2.36p (s, 3h), 3.84 (s, 3h), 4.33 (s, 2h), 6.9 (d, 2h, J=9.2 Hz), 7.9 (d, 2h, J=9.2 Hz).

Workup

  1. customhad formed
  2. filtrationwas filtered
  3. customthe ethanol removed at reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane (250 ml)
  5. washwashed with water (200 ml), brine (200 ml)
  6. dry with materialdried over Na2SO4
  7. customthe solvent removed at reduced pressure
  8. customThe resulting residue was chromatographed on silica with a gradient from 10%-35% ethyl acetate in hexane

Sources & evidence

ORD record
ord-4be9e9363e5d434d8977993494254f6f
Source dataset
uspto-grants-2002_12
Patent number
US06492413B2

Reaction notes

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