1,2-Dibromoethane → 1-{2-[4-(2-Bromoethoxy)naphthalen-1-yl]-1-benzofuran-3-yl}ethan-1-one

HRID 1287931Notes

Reaction equation

HRID 1287931 reaction equation
[C:1]([C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][C:5]=1[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([OH:23])=[CH:15][CH:14]=1)(=[O:3])[CH3:2].[Br:24][CH2:25][CH2:26]Br.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[C:1]([C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][C:5]=1[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([O:23][CH2:26][CH2:25][Br:24])=[CH:15][CH:14]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 215070471-[2-(4-Hydroxynaphthalen-1-yl)-1-benzofuran-3-yl]ethan-1-one

Product 1

HCID 215070481-{2-[4-(2-Bromoethoxy)naphthalen-1-yl]-1-benzofuran-3-yl}ethan-1-one

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of 11.9 g. (0.039 mol.) of 3-acetyl-2-(4-hydroxynaphthyl)benzofuran in 400 ml. of 2-butanone was added 100 ml. (0.24 mol.) of 1,2-dibromoethane and 22 g. (0.16 mol.) of anhydrous potassium carbonate. The reaction mixture was refluxed for 8 hours, then the solvent was evaporated and the excess 1,2-dibromoethane was removed by distillation in vacuo. The residue was chromatographed on silica with 10% hexane in methylene chloride as eluant to give 3-acetyl-2-[4-(2-bromoethoxy)naphthyl]benzofuran, m.p. 115°-117°.

Workup

  1. temperatureThe reaction mixture was refluxed for 8 hours
  2. customthe solvent was evaporated
  3. customthe excess 1,2-dibromoethane was removed by distillation in vacuo
  4. customThe residue was chromatographed on silica with 10% hexane in methylene chloride as eluant

Sources & evidence

ORD record
ord-287efd63087a4e40bbc6a7bab5126e9f
Source dataset
uspto-grants-1976_10
Patent number
US03985896

Reaction notes

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