Trimethyl borate → (4-Fluoro-3-methoxyphenyl)boronic acid

HRID 1515504Notes

Reaction equation

HRID 1515504 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([O:9][CH3:10])[CH:3]=1.[Li]CCCC.[B:16](OC)([O:19]C)[O:17]C>C1COCC1>[CH3:10][O:9][C:4]1[CH:3]=[C:2]([B:16]([OH:19])[OH:17])[CH:7]=[CH:6][C:5]=1[F:8]

Participants

5

Reactant 3

HCID 8470Trimethyl borateHCID 136049094-Bromo-1-fluoro-2-methoxybenzeneHCID 178418339Butyllithium

Product 1

HCID 44558185(4-Fluoro-3-methoxyphenyl)boronic acidYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7B (2.7 g, 13.1 mmol) in THF (25 mL) at −78° C. was added n-BuLi (1.6 M in hexanes, 11.0 mL, 17.7 mmol). The mixture was stirred at −78° C. for 40 min before trimethyl borate (2.7 mL, 24.3 mmol) was added. The reaction was left stirring from −78° C. to rt over 18 h. It was quenched with 1.0 N HCl (40 mL), extracted with EtOAc, washed with brine and dried over Na2SO4. After evaporation of the solvent, the crude solid product was triturated with EtOAc/hexanes (1:4). After filtration, 7C (0.75 g, 35% yield) was collected as a white solid. 1H NMR (400 MHz, Methanol-d4) δ ppm 3.86 (s, 3H) 7.03-7.45 (m, 3H).

Workup

  1. additionwas added
  2. waitThe reaction was left
  3. customIt was quenched with 1.0 N HCl (40 mL)
  4. extractionextracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customAfter evaporation of the solvent
  8. customthe crude solid product was triturated with EtOAc/hexanes (1:4)

Sources & evidence

ORD record
ord-c2cbb3e13c514fdb8c10dedec2d26ad6
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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