Bromine → 1-Methoxycarbonylmethoxy-5-oxo-6-bromo-5,6,7,8-tetrahydronaphthalene

HRID 276934Notes

Reaction equation

HRID 276934 reaction equation
[CH3:1][O:2][C:3]([CH2:5][O:6][C:7]1[C:16]2[CH2:15][CH2:14][CH2:13][C:12](=[O:17])[C:11]=2[CH:10]=[CH:9][CH:8]=1)=[O:4].[Br:18]Br>ClCCl>[CH3:1][O:2][C:3]([CH2:5][O:6][C:7]1[C:16]2[CH2:15][CH2:14][CH:13]([Br:18])[C:12](=[O:17])[C:11]=2[CH:10]=[CH:9][CH:8]=1)=[O:4]

Participants

4

Reactant 2

HCID 24408BromineHCID 141811861-Methoxycarbonylmethoxy-5-oxo-5,6,7,8-tetrahydronaphthalene

Product 1

HCID 226291671-Methoxycarbonylmethoxy-5-oxo-6-bromo-5,6,7,8-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-methoxycarbonylmethoxy-5-oxo-5,6,7,8-tetrahydronaphthalene (0.5 g) in dry dichloromethane (3 ml) was added bromine (0.14 ml) at 0° C. The mixture was warmed up to room temperature, stirred for 2 hours. The mixture was washed with an aqueous saturated sodium bicarbonate, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (30 ml) using a mixture of dichloromethane-n-hexane. The desired fractions were collected and evaporated in vacuo to give 1-methoxycarbonylmethoxy-5-oxo-6-bromo-5,6,7,8-tetrahydronaphthalene (0.41 g). The crude crystal (50 mg) was recrystallized from ethyl acetate-n-hexane to give 31 mg as a white crystal.

Workup

  1. washThe mixture was washed with an aqueous saturated sodium bicarbonate
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was chromatographed on silica gel (30 ml)
  5. additiona mixture of dichloromethane-n-hexane
  6. customThe desired fractions were collected
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-129f58d5aff944af92c3a54a5b479609
Source dataset
uspto-grants-2002_03
Patent number
US06355640B1

Reaction notes

Loading…