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

HRID 1254311Notes

Reaction equation

HRID 1254311 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-1549fb9b14664a17babf9cd34b1e7fa0
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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