Bromine → HCID 22995025, compound

HRID 1168041Notes

Reaction equation

HRID 1168041 reaction equation
[CH3:1][C:2]12[CH2:13][CH2:12][C:9]([CH3:14])([CH2:10][CH2:11]1)[C:8]1[CH:7]=[CH:6][C:5]([OH:15])=[CH:4][C:3]2=1.[Br:16]Br>C(O)(=O)C>[Br:16][C:6]1[C:5]([OH:15])=[CH:4][C:3]2[C:2]3([CH3:1])[CH2:13][CH2:12][C:9]([CH3:14])([C:8]=2[CH:7]=1)[CH2:10][CH2:11]3

Participants

4

Reactant 2

HCID 24408BromineHCID 22995028HCID 22995028, compound2×

Product 1

HCID 22995025HCID 22995025, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 1,8-dimethyltricyclo[6.2.2.02,7]dodeca-2(7),3,5-trien-4-ol (Compound 2, 1.58 g, 7.81 mmol) in 10 mL of glacial acetic acid was added bromine (0.40 mL, 7.81 mmol). The reaction mixture was stirred at 25° C. for 4 hours then quenched with 10% Na2S2O3 and extracted with Et2O. The combined ether extracts were washed with water and brine, and dried over Na2SO4, and filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using ethyl acetate:hexane (2:98) to yield the title compound as a yellow oil.

Workup

  1. customthen quenched with 10% Na2S2O3
  2. extractionextracted with Et2O
  3. washThe combined ether extracts were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-3a8e9076f6ce4ac48fa14ddfa23e0d0d
Source dataset
uspto-grants-2003_09
Patent number
US06620963B1

Reaction notes

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