4-Bromophenacyl bromide → 1-(4-Bromophenyl)-2-[(3-methoxyphenyl)sulfanyl]ethan-1-one

HRID 347155Notes

Reaction equation

HRID 347155 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.[OH-].[K+].[CH:12]1[C:17]([C:18]([CH2:20]Br)=[O:19])=[CH:16][CH:15]=[C:14]([Br:22])[CH:13]=1.CCOC(C)=O>C(O)C.O>[Br:22][C:14]1[CH:15]=[CH:16][C:17]([C:18](=[O:19])[CH2:20][S:1][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=2)=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 74544-Bromophenacyl bromideHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 849893-Methoxybenzenethiol

Product 1

HCID 154226451-(4-Bromophenyl)-2-[(3-methoxyphenyl)sulfanyl]ethan-1-oneYield 105.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

10.09 g (70.5 mmol) 3-mercaptoanisole were added to a freshly prepared solution of 4.6 g (70.5 mmol) KOH in 75 ml ethanol and 30 ml water. Over a period of 30 min, 20.0 g (70.5 mmol) 2,4-dibromoacetophenone in 150 EtOAc were added at 0° C. and the solution was stirred at RT over night. The suspension was concentrated and dissolved in EtOAc and water. The inorganic phase was extracted with EtOAC, the combined organic phases were washed with water and brine and dried over Na2SO4. Evaporation yielded 25.1 g (quant) 1-(4-Bromo-phenyl)-2-(3-methoxy-phenylsulfanyl)-ethanone as white crystalline, MS: 336 (M, 1Br). (In analogy to Jones, Charles D.; Jevnikar, Mary G.; Pike, Andrew J.; Peters, Mary K.; Black, Larry J.; Thompson, Allen R.; Falcone, Julie F.; Clemens, James A. Antiestrogens. 2. Structure-activity studies in a series of 3-aroyl-2-arylbenzo[b]thiophene derivatives leading to [6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl]-[4-[2-(1-piperidinyl)ethoxy]phenyl]methanone hydrochloride (LY 156758), a remarkably effective estrogen antagonist with only minimal intrinsic estrogenicity. J. Med. Chem. (1984), 27(8), 1057–66.)

Workup

  1. concentrationThe suspension was concentrated
  2. dissolutiondissolved in EtOAc
  3. extractionThe inorganic phase was extracted with EtOAC
  4. washthe combined organic phases were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. customEvaporation

Sources & evidence

ORD record
ord-60bb364abd7649b9b634f346871da2fd
Source dataset
uspto-grants-2007_02
Patent number
US07173043B2

Reaction notes

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