Trimethyl borate → (2-Fluoro-5-methoxy-4-methylphenyl)boronic acid

HRID 1438167Notes

Reaction equation

HRID 1438167 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7](I)[C:6]([F:10])=[CH:5][C:4]=1[CH3:11].[Li]CCCC.[B:17](OC)([O:20]C)[O:18]C>C1COCC1>[CH3:1][O:2][C:3]1[C:4]([CH3:11])=[CH:5][C:6]([F:10])=[C:7]([B:17]([OH:20])[OH:18])[CH:8]=1

Participants

5

Reactant 3

HCID 8470Trimethyl borateHCID 210705041-Fluoro-2-iodo-4-methoxy-5-methylbenzeneHCID 178418339Butyllithium

Product 1

HCID 57942889(2-Fluoro-5-methoxy-4-methylphenyl)boronic acidYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 122D (750 mg, 2.8 mmol) in THF (10 mL) was added n-BuLi (1.6M in hexane, 2.3 mL) at −78° C. After stirring for 10 min, trimethyl borate (0.63 mL) was introduced. The mixture was stirred from −78° C. to rt for 3 h before it was quenched by 1N HCl and extracted with ethyl acetate. The organic extracts were washed with saturated Na2S2O3, brine and dried over MgSO4. Evaporation of the solvent gave product 122E (356 mg, 69% yield) as a solid. 1H NMR (400 MHz, CDCl3) δ ppm 2.18 (s, 3H) 3.80 (s, 3H) 6.80-6.86 (m, 2H).

Workup

  1. stirringThe mixture was stirred from −78° C. to rt for 3 h before it
  2. customwas quenched by 1N HCl
  3. extractionextracted with ethyl acetate
  4. washThe organic extracts were washed with saturated Na2S2O3, brine
  5. dry with materialdried over MgSO4
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-b1e4e4c6b4cd4209be662eebae283132
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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