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

HRID 481211

Reaction equation

HRID 481211 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, 1.6 M 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×). 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×)
  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-fda1febec8664fc997aba847fc6afbd9
Source dataset
uspto-grants-2003_11
Patent number
US06653483B1

Linked notes

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