Chloroform → 1-(2-Bromoethenyl)-4-methoxynaphthalene

HRID 1287928Notes

Reaction equation

HRID 1287928 reaction equation
C([CH:4]=[CH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([O:16][CH3:17])=[CH:8][CH:7]=1)(O)=O.C(Cl)(Cl)Cl.[Br:22]Br.C(=O)([O-])[O-].[Na+].[Na+]>O.C(Cl)Cl>[Br:22][CH:4]=[CH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([O:16][CH3:17])=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 10340Sodium CarbonateHCID 24408BromineHCID 38801493-(4-methoxynaphthyl)acrylic acid

Product 1

HCID 544133521-(2-Bromoethenyl)-4-methoxynaphthalene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 33.3 g. (0.146 mol.) of 1-(2-carboxyethenyl)-4-methoxynaphthalene in 500 ml. of chloroform was added dropwise a solution of 8.05 ml. (0.146 mol.) of bromine in 125 ml. of methylene chloride. The solvent was removed, a solution of 31 g. (0.292 mol.) of sodium carbonate in 300 ml. of water was added to the residue and the mixture was refluxed for 2 hours. After cooling, the mixture was extracted with methylene chloride, the layers were separated and the organic phase was washed with water and saturated sodium chloride solution, dried (MgSO4) and evaporated to dryness to give 1-(2-bromoethenyl)-4-methoxynaphthalene.

Workup

  1. additionTo a suspension of 33.3 g
  2. customThe solvent was removed
  3. temperaturethe mixture was refluxed for 2 hours
  4. temperatureAfter cooling
  5. extractionthe mixture was extracted with methylene chloride
  6. customthe layers were separated
  7. washthe organic phase was washed with water and saturated sodium chloride solution
  8. dry with materialdried (MgSO4)
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-6f2f20a1e221434ab754b98afa291f7a
Source dataset
uspto-grants-1976_10
Patent number
US03985896

Reaction notes

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