Potassium Hydroxide → 1-Bromo-3-[(2,2-diethoxyethyl)sulfanyl]benzene

HRID 2355431Notes

Reaction equation

HRID 2355431 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.[OH-].[K+].[CH2:11]([O:13][CH:14]([O:17][CH2:18][CH3:19])[CH2:15]Br)[CH3:12]>CS(C)=O.O.CCOCC>[Br:1][C:2]1[CH:3]=[C:4]([S:8][CH2:15][CH:14]([O:17][CH2:18][CH3:19])[O:13][CH2:11][CH3:12])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 80597m-Bromobenzenethiol

Product 1

HCID 218165781-Bromo-3-[(2,2-diethoxyethyl)sulfanyl]benzeneYield 103.7%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 3-bromothiophenol (5.0 g, 26 mmol) in DMSO (40 mL) was added a solution of KOH pellets (85% by wt, 2.15 g, 32 mmol) in water (4 mL) followed by bromoacetaldehyde diethyl acetal (4.5 mL, 29 mmol). The mixture was stirred at rt for 5 d, diluted with ether (300 mL) and washed with water (3×100 mL). The combined water washes were extracted with ether (100 mL). The combined ether extracts were washed with brine (100 mL), dried over MgSO4 and concentrated to afford (3-bromophenyl)(2,2-diethoxyethyl)sulfane (8.23 g, 100%) as a colorless oil.

Workup

  1. washwashed with water (3×100 mL)
  2. extractionThe combined water washes were extracted with ether (100 mL)
  3. washThe combined ether extracts were washed with brine (100 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e7777b69737c4fcf8317ace4037547c4
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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