Dichloromethane → HCID 22490886, compound

HRID 2180553Notes

Reaction equation

HRID 2180553 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12]C)[CH:8]([CH3:14])[CH:7](C)[CH2:6][CH2:5]2.B(Br)(Br)Br.Cl[CH2:21]Cl>>[Br:1][C:2]1[C:11]([OH:12])=[CH:10][C:9]2[C:8]([CH3:14])([CH3:21])[CH2:7][CH2:6][CH2:5][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 22490924HCID 22490924, compound

Product 1

HCID 22490886HCID 22490886, compound

Conditions

Temperature
0 °C

Procedure

To 6-bromo-7-methoxy-1,2-dimethyl-1,2,3,4-tetrahydro-naphthalene (Compound A-1 ([U.S. Pat. No. 6,613,917, incorporated herein by reference), 6.34 g, 23.56 mmol) in dichloromethane (10 mL) at −30° C. was added a solution of boron tribromide (1.0 M in dichloromethane, 47 mL, 47 mmol). After warming to 0° C. over 1 h, the reaction mixture was quenched carefully with ice water and extracted with ether. The organic layer was washed successively with water, brine, dried over Na2SO4, and concentrated in vacuo. Purification by flash column chromatography (silica gel, 5% ethyl acetate/hexane) yielded the title compound as a white solid.

Workup

  1. customthe reaction mixture was quenched carefully with ice water
  2. extractionextracted with ether
  3. washThe organic layer was washed successively with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification by flash column chromatography (silica gel, 5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-94385a19c02848aa995f0a9e4fa356d1
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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