Acetic Acid → HCID 14580198, compound

HRID 2372653Notes

Reaction equation

HRID 2372653 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[CH:6]=1)=[O:4].[C:12]1([S:18]([CH3:21])(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O)(=O)C.O>C1COCC1.CCOCC>[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[CH:6]=1)([OH:4])[CH2:21][S:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:20])=[O:19]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 18369Methyl phenyl sulfoneHCID 5195852-Bromo-1-(3-bromophenyl)ethan-1-one

Product 1

HCID 14580198HCID 14580198, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

In a manner identical with Example 57, 2,3'-dibromoacetophenone (7.8 g, 0.028 mole) is treated with 1 equivalent of the magnesium anion of methyl phenyl sulphone in THF at -70° C. The mixture is stirred for 2 h at -70° C., acetic acid (7 cc) is then added and the mixture is poured into water (100 g). It is reextracted with ether (3×100 cc), is washed with brine (2×100 cc) and is dried over MgSO4. The crude is precipitated with ether (50 cc) with warming and recrystallized from isopropyl ether to give white crystals of 1-bromo-2-[3'-bromophenyl]-3-phenylsulphonyl-2-propanol (2.4 g, 20%). Mp=132° C.

Workup

  1. washis washed with brine (2×100 cc)
  2. dry with materialis dried over MgSO4
  3. customThe crude is precipitated with ether (50 cc)
  4. temperaturewith warming
  5. customrecrystallized from isopropyl ether

Sources & evidence

ORD record
ord-44f70c0a0ced4c0b87ca341a6b721166
Source dataset
uspto-grants-1992_03
Patent number
US05100460

Reaction notes

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