Hydrochloric Acid → 4-Cyclopropylbenzeneboronic acid

HRID 2284467Notes

Reaction equation

HRID 2284467 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.[B:18](OC(C)C)([O:23]C(C)C)[O:19]C(C)C.Cl>CCCCCC.C1COCC1>[CH:8]1([C:5]2[CH:6]=[CH:7][C:2]([B:18]([OH:23])[OH:19])=[CH:3][CH:4]=2)[CH2:10][CH2:9]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 21531Triisopropyl borateHCID 122213551-Bromo-4-cyclopropylbenzene

Product 1

HCID 28494284-Cyclopropylbenzeneboronic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-20 °C

Procedure

2.5 M solution of nButyllithium in hexane (14.5 mL) is added dropwise to 1-bromo-4-cyclopropyl-benzene (5.92 g) dissolved in THF (14 mL) and toluene (50 mL) and chilled to −70° C. The resultant solution is stirred at −70° C. for 30 min before triisopropyl borate (8.5 mL) is added. The solution is warmed to −20° C. and then treated with 4 M aqueous hydrochloric acid (15.5 mL). The reaction mixture is further warmed to room temperature and then the organic phase is separated. The aqueous phase is extracted with ethyl acetate and the combined organic phases are dried (sodium sulfate). The solvent is evaporated and the residue is washed with a mixture of ether and cyclohexane to give the product as a colorless solid.

Workup

  1. additionis added
  2. temperatureThe reaction mixture is further warmed to room temperature
  3. customthe organic phase is separated
  4. extractionThe aqueous phase is extracted with ethyl acetate
  5. dry with materialthe combined organic phases are dried (sodium sulfate)
  6. customThe solvent is evaporated
  7. washthe residue is washed with a mixture of ether and cyclohexane

Sources & evidence

ORD record
ord-8569aed9cb53473fac9aaf663837f8a4
Source dataset
uspto-grants-2015_09
Patent number
US09145434B2

Reaction notes

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