Triisopropyl borate → (5,6,7,8-Tetrahydro-5,5-dimethylnaphth-2-yl)boronic acid

HRID 1289309Notes

Reaction equation

HRID 1289309 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[CH2:7][CH2:6][CH2:5]2.[Li]CCCC.C([O:22][B:23](OC(C)C)[O:24]C(C)C)(C)C>C1(C)C=CC=CC=1.Cl>[CH3:12][C:8]1([CH3:13])[CH2:7][CH2:6][CH2:5][C:4]2[CH:3]=[C:2]([B:23]([OH:24])[OH:22])[CH:11]=[CH:10][C:9]1=2

Participants

6

Reactant 3

HCID 21531Triisopropyl borateHCID 105860636-Bromo-1,1-dimethyl-1,2,3,4-tetrahydronaphthaleneHCID 178418339Butyllithium

Product 1

HCID 22571498(5,6,7,8-Tetrahydro-5,5-dimethylnaphth-2-yl)boronic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

To a cold (-78° C.) solution of 2.02 g (8.4 mmol) of 6-bromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene in 11.0 mL of toluene, was added 4.6 g (6.8 mL, 10.9 mmol, 1.6M in hexane) of n-BuLi. The resulting solution was stirred at -78° C. for 45 min. and then 2.40 g (3.0 mL, 12.7 mmol) of triisopropylborate was dropwise added and the reaction stirred at room temperature for 12 h. The reaction was then diluted with 10% HCl, and extracted with ether (2 x). The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give an oil. Recrystallization from hexane afforded the title compound as a white solid.

Workup

  1. stirringthe reaction stirred at room temperature for 12 h
  2. extractionextracted with ether (2 x)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give an oil
  7. customRecrystallization from hexane

Sources & evidence

ORD record
ord-e1ec370d0a684745a94eba6d8640f4a3
Source dataset
uspto-grants-1998_05
Patent number
US05747542

Reaction notes

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