Bromine → HCID 22218307, compound

HRID 1795605Notes

Reaction equation

HRID 1795605 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][C:10]2([CH3:14])[CH3:13])=[CH:5][CH:4]=1.[Br:15]Br>C(O)(=O)C>[Br:15][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:3]=1[O:2][CH3:1])[C:10]([CH3:14])([CH3:13])[CH2:9][CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 24408BromineHCID 124151467-Methoxy-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 22218307HCID 22218307, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 7-methoxy-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene (0.99 g, 5.2 mmol) in glacial acetic acid (30 mL) at 0° C. was added slowly bromine (0.5 mL, 10.4 mmol), and the resulting solution was allowed to slowly warm to room temperature while being stirred. After 48 h, the reaction mixture was quenched with a saturated solution of Na2S2O3 and extracted with ethyl acetate, and the combined extracts were dried (MgSO4). The solvent was removed under reduced pressure, and the residue was purified by flash column (hexane:ethyl acetate=95:5) to afford 0.5556g (40%) of the title compound as a clear oil.

Workup

  1. customthe reaction mixture was quenched with a saturated solution of Na2S2O3
  2. extractionextracted with ethyl acetate
  3. dry with materialthe combined extracts were dried (MgSO4)
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by flash column (hexane:ethyl acetate=95:5)

Sources & evidence

ORD record
ord-624290c422db4d5aa8f6396b46c67403
Source dataset
uspto-grants-2006_04
Patent number
US07026487B2

Reaction notes

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