Boron tribromide → HCID 86700505, compound

HRID 1499986Notes

Reaction equation

HRID 1499986 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13]C)[C:9]([CH3:16])([CH3:15])[CH2:8][CH2:7][C:6]2([CH3:18])[CH3:17].B(Br)(Br)Br>C(Cl)Cl>[CH3:17][C:6]1([CH3:18])[CH2:7][CH2:8][C:9]([CH3:15])([CH3:16])[C:10]2[CH:11]=[C:12]([OH:13])[C:3]([OH:2])=[CH:4][C:5]1=2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 2267066,7-dimethoxy-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 86700505HCID 86700505, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,2,3,4-tetrahydro-6,7-dimethoxy-1,1,4,4-tetramethylnaphthalene (Example 1, 0.7 g, 2.82 mmol) was dissolved in anhydrous CH2Cl2. At −78° C., BBr3 (2.96 mL, 2.96 mmol, 1.0M in CH2Cl2) was slowly added. The reaction mixture was allowed to warm up to room temperature and stir for 30 minutes before being quenched with ice water. The layers were separated, and the aqueous layer extracted three times with CH2Cl2. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to provide the title compound. 1H NMR (CDCl3): 1.22 (s, 12H), 1.64 (s, 4H), 4.98 (s, 2H, —OH), 6.78 (s, 2H). This compound was used in the next step without further purification.

Workup

  1. custombefore being quenched with ice water
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted three times with CH2Cl2
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a7c763ddf9d94621beae87b2d6e4fb0a
Source dataset
uspto-grants-2015_12
Patent number
US09203112B2

Reaction notes

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