Hydrochloric Acid → 3-Isopropylbenzeneboronic acid

HRID 2384006Notes

Reaction equation

HRID 2384006 reaction equation
[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH:13]([CH3:15])[CH3:14])[CH:8]=1.C([O:19][B:20](OC(C)C)[O:21]C(C)C)(C)C.Cl>C1COCC1>[CH:13]([C:9]1[CH:8]=[C:7]([B:20]([OH:21])[OH:19])[CH:12]=[CH:11][CH:10]=1)([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 1384991-Bromo-3-isopropylbenzeneHCID 178418339Butyllithium

Product 1

HCID 27734783-Isopropylbenzeneboronic acidYield 93.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

n-BuLi (7.7 mL, 14.0 mmol) was added dropwise to a stirred solution of 1-bromo-3-isopropyl-benzene (2.4 g, 12.1 mmol) in dry THF (40 mL) over 30 min at −70° C. under nitrogen. The reaction mixture was degassed for 15 min, and triisopropylborate (2.63 g, 14.0 mmol) was added at the same temperature. The reaction mixture was gradually warmed to 0° C. during 90 min and stirred for an additional 30 min at 0° C. The reaction mixture was then cooled to −20° C., and an aqueous solution of 2N HCl (20 mL) was added slowly. THF was distilled off and the reaction mixture was extracted with ethyl acetate (2×20 mL). The combined organic layers were dried over Na2SO4, and concentrated in vacuo to obtain the crude product (1.85 g, 93.5%), which was used for the next step without further purification.

Workup

  1. customThe reaction mixture was degassed for 15 min
  2. temperatureThe reaction mixture was then cooled to −20° C.
  3. distillationTHF was distilled off
  4. extractionthe reaction mixture was extracted with ethyl acetate (2×20 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fd1ff9c0ecbd4f2ea6b64bbf3f5318db
Source dataset
uspto-grants-2012_09
Patent number
US08263656B2

Reaction notes

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