Iodine → 2-(Benzyloxy)-4-methoxyphenylboronic acid

HRID 1857563Notes

Reaction equation

HRID 1857563 reaction equation
[Mg].II.[CH2:4]([O:11][C:12]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=1Br)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[B:21](OC)([O:24]C)[O:22]C>C1COCC1.C(OCC)C.CCCCCC>[CH2:4]([O:11][C:12]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=1[B:21]([OH:24])[OH:22])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 807IodineHCID 8470Trimethyl borateHCID 5462224MagnesiumHCID 184340291-Bromo-4-methoxy-2-phenylmethoxybenzene

Product 1

HCID 118320852-(Benzyloxy)-4-methoxyphenylboronic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 21584099Diethylether hexaneSolvent

Procedure

To a stirred and gently refluxing suspension of magnesium powder (382 mg, 15.7 mmol) in THF (10 ml) containing a few crystals of iodine, was added dropwise, a solution of 2-benzyloxy-1-bromo-4-methoxybenzene (WO 93/08799, 4.39 g, 15.0 mmol) in THF (40 ml). After completion of the addition, the mixture was refluxed for 1.25 hours, cooled and then transferred via a canula to a stirred solution of trimethyl borate (3.11 g, 3.40 ml, 30.0 mmol) in THF (25 ml) at -78° C. The mixture was stirred at -78° C. for 30 minutes and then the cooling bath was removed and stirring was continued at room temperature for a further 2 hours. The mixture was partitioned between diethyl ether and 1 N HCl (200 ml) and the product was extracted into diethyl ether. The extracts were washed with water, dried (MgSO4) and concentrated to give a yellow solid. Trituration with warm diethyl ether/n-hexane gave after drying the title compound as a cream solid. Yield 2.159 g (56%).

Workup

  1. temperaturegently refluxing
  2. additionwas added dropwise
  3. additionAfter completion of the addition
  4. temperaturethe mixture was refluxed for 1.25 hours
  5. temperaturecooled
  6. stirringThe mixture was stirred at -78° C. for 30 minutes
  7. customthe cooling bath was removed
  8. stirringstirring
  9. customThe mixture was partitioned between diethyl ether and 1 N HCl (200 ml)
  10. extractionthe product was extracted into diethyl ether
  11. washThe extracts were washed with water
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated
  14. customto give a yellow solid
  15. dry with materialafter drying the title compound as a cream solid

Sources & evidence

ORD record
ord-7be2ef9c3b7d46b79bcfb185e1f89334
Source dataset
uspto-grants-2000_11
Patent number
US06147111

Reaction notes

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