Water → HCID 12398618, compound

HRID 1583346Notes

Reaction equation

HRID 1583346 reaction equation
C([Li])CCC.Br[C:7]1[S:11][C:10]2[CH:12]=[C:13]([CH3:16])[CH:14]=[CH:15][C:9]=2[C:8]=1[Br:17].O>CCOCC>[Br:17][C:8]1[C:9]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:10]=2[S:11][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 13662968HCID 13662968, compoundHCID 178418339Butyllithium

Product 1

HCID 12398618HCID 12398618, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of n-butyl lithium (22.3 ml. of 1.6M solution in hexane) was added dropwise to a stirred solution of 2,3-dibromo-6-methylbenzo[b]thiophene (11.76 g.) in dry ether (150 ml.) at 0° under an atmosphere of dry nitrogen. The resulting solution was stirred at 0° for 1 hour and then water (50 ml.) was added. The mixture was stirred for a few minutes and then the ether layer was separated, dried (Na2SO4) and evaporated to give an oil. The oil was distilled to give 3-bromo-6-methylbenzo[b]thiophene (5.80 g.), b.p. 112°-114° C. @ 0.2 m.m., m.p. 51°-53° C. (from methanol).

Workup

  1. stirringThe mixture was stirred for a few minutes
  2. customthe ether layer was separated
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customto give an oil
  6. distillationThe oil was distilled

Sources & evidence

ORD record
ord-9a2c1d42aac2488aa506a2e9ab2e7ec8
Source dataset
uspto-grants-1985_11
Patent number
US04551468

Reaction notes

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