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Trimethyl borate → (2-Chloro-5-isopropylphenyl)boronic acid

HRID 604599
Notes
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Reaction equation

HRID 604599 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[Cl:11].C([Li])CCC.[B:17](OC)([O:20]C)[O:18]C>C1COCC1>[Cl:11][C:3]1[CH:4]=[CH:5][C:6]([CH:8]([CH3:10])[CH3:9])=[CH:7][C:2]=1[B:17]([OH:20])[OH:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8470Trimethyl borateHCID 509978642-Bromo-1-chloro-4-isopropylbenzeneHCID 178418339Butyllithium

Product 1

HCID 57509290(2-Chloro-5-isopropylphenyl)boronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-bromo-1-chloro-4-isopropylbenzene (0.37 g, 1-59 mmol) in dry THF (5 mL) at −78° C., n-butyl lithium (0.76 mL, 1.90 mmol, 2.5 M) was added. The solution was stirred at −78° C. for 30 min. Trimethyl borate (0.53 mL, 4.76 mmol) was added. The solution was stirred at −78° C. for 2.5 h. The reaction was quenched with saturated aqueous NH4Cl. The aqueous layer was extracted with EtOAc (3×15 mL). The combined EtOAc layers were dried over Na2SO4. The residue was used without further purification after evaporation of the solvent.

Workup

  1. stirringThe solution was stirred at −78° C. for 2.5 h
  2. customThe reaction was quenched with saturated aqueous NH4Cl
  3. extractionThe aqueous layer was extracted with EtOAc (3×15 mL)
  4. dry with materialThe combined EtOAc layers were dried over Na2SO4
  5. customThe residue was used without further purification
  6. customafter evaporation of the solvent

Sources & evidence

ORD record
ord-825e77c2745847b698af8325c8d8247c
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07910592B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes