N,N-Diethylaniline → 5-Bromo-2-methyl-1-benzothiophene

HRID 330282Notes

Reaction equation

HRID 330282 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([S:6][CH2:7][C:8](Cl)=C)=[CH:4][CH:3]=1.[CH2:13](N(CC)C1C=CC=CC=1)C>CCOCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:6][C:7]([CH3:8])=[CH:13][C:11]=2[CH:12]=1

Participants

4

Reactant 2

HCID 7061N,N-DiethylanilineHCID 14819351(4-Bromophenyl)(2-chloroallyl)sulfane

Product 1

HCID 136630355-Bromo-2-methyl-1-benzothiopheneYield 46%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

According to the procedure of W. K. Anderson, J. Chem. Soc., Perkin, 1, 1 (1976), a mixture of 3-(4-bromothiophenoxy)-2-chloro-1-propene (37.4 g, 0.142 mol) and N,N-diethylaniline (180 mL) was heated to 210°-215° C. for 2 days, cooled, and diluted with ether. The ethereal layer was washed with 10% HCl (3×200 mL), dried (MgSO4), and concentrated. Purification by column chromatography (eluant: hexane) gave 15.0 g (46%) of product as a white solid.

Workup

  1. temperaturewas heated to 210°-215° C. for 2 days
  2. temperaturecooled
  3. washThe ethereal layer was washed with 10% HCl (3×200 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customPurification by column chromatography (eluant: hexane)

Sources & evidence

ORD record
ord-df1be2fa6fdf4514b1cfc191a598f30a
Source dataset
uspto-grants-1990_01
Patent number
US04895860

Reaction notes

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