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

HRID 2266231Notes

Reaction equation

HRID 2266231 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-01e85598fd3144a8afc97228f9ea49ef
Source dataset
uspto-grants-2010_12
Patent number
US07858624B2

Reaction notes

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