Trimethyl borate → HCID 86710642, compound

HRID 1027235Notes

Reaction equation

HRID 1027235 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[C:10]=1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.C[O:24][B:25](OC)[O:26]C>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[C:10]=1[B:25]([OH:26])[OH:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8470Trimethyl borateHCID 86710641HCID 86710641, compoundHCID 178418339Butyllithium

Product 1

HCID 86710642HCID 86710642, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a mixture of 1-(benzyloxy)-2-bromo-3-methoxybenzene (2.66 g, 9.07 mmol) in THF (20 mL) was added butyllithium (2.5 M in THF, 4 mL, 9.98 mmol) at −78° C. dropwise over 15 minutes. The mixture was stirred at −78° C. for 30 minutes, then trimethylborate (4.0 mL, 36.3 mmol) was added. The mixture was allowed to warm to RT and stirred overnight. The mixture was quenched with 1 M aqueous HCl to pH 2 and extracted with DCM. The organic phase was dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography (EtOAc/Heptane) to afford the desired product as a white solid (1.07 g, 46% yield). MS (M+1)=259.4.

Workup

  1. temperatureto warm to RT
  2. stirringstirred overnight
  3. customThe mixture was quenched with 1 M aqueous HCl to pH 2
  4. extractionextracted with DCM
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography (EtOAc/Heptane)

Sources & evidence

ORD record
ord-a4cdea72a0ac4c70a7f9d37290b6b532
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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