Bromine → HCID 22218307, compound

HRID 1166669Notes

Reaction equation

HRID 1166669 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 0.5556 g (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-e2451608d3a0418497956f3a4e2070aa
Source dataset
uspto-grants-2003_09
Patent number
US06613917B1

Reaction notes

Loading…