Diethyl Ether → HCID 58746591, compound

HRID 724601Notes

Reaction equation

HRID 724601 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:10]=2)=[CH:5][CH:4]=1.[C:19]([O-:22])(=[S:21])[CH3:20].[K+].C(OCC)C>CN(C)C=O>[CH3:18][S:15]([C:11]1[CH:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][S:21][C:19](=[O:22])[CH3:20])=[CH:4][CH:5]=2)[CH:14]=[CH:13][CH:12]=1)(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21878563HCID 21878563, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 58746591HCID 58746591, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4′-bromomethyl-3-methylsulfonylbiphenyl (190 mg, 0.57 mmol) (WO 01/70753) and potassium thioacetate (78 mg, 0.68 mmol) in N,N-dimethylformamide (4 mL) was heated at 150° C. in a microwave for 3 min. The reaction mixture was poured into diethyl ether (30 mL) and washed with water (3×15 mL), brine (15 mL), dried with magnesium sulfate, filtered, and concentrated to give a crude yellow oil. The crude oil was purified by flash column chromatography to yield 1.35-A (180 mg, 89%) as a thick light yellow oil. LCMS found for C16H17O3S2 (M+H)+: m/z=321.

Workup

  1. washwashed with water (3×15 mL), brine (15 mL)
  2. dry with materialdried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude yellow oil
  6. customThe crude oil was purified by flash column chromatography

Sources & evidence

ORD record
ord-4ba2c975f27248c7857301041196dd4f
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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