Hydrochloric Acid → HCID 67467385, compound

HRID 2171009Notes

Reaction equation

HRID 2171009 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH3:11])[C:3]=1[O:12][CH2:13][CH:14]([CH3:16])[CH3:15].[Li]CCCC.[B:22](OC)([O:25]C)[O:23]C.[NH4+].[Cl-].Cl>C1COCC1>[CH3:11][O:10][C:4]1[C:3]([O:12][CH2:13][CH:14]([CH3:16])[CH3:15])=[C:2]([B:22]([OH:25])[OH:23])[CH:7]=[CH:6][C:5]=1[O:8][CH3:9]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 25517Ammonium ChlorideHCID 67466253HCID 67466253, compoundHCID 178418339Butyllithium

Product 1

HCID 67467385HCID 67467385, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere 1-bromo-2-isobutoxy-3,4-dimethoxy-benzene (6.7 g, 23.2 mmol) was dissolved in dry THF (50 mL). The solution was cooled to −70° C. while n-BuLi (2.0 M in pentane, 12.8 mL, 25.5 mmol) was added over 10 min. The solution was stirred for 20 min at −70° C. after which trimethyl borate (5.2 mL, 46.4 mmol) was added over 10 min. The solution was kept at −70° C. for 15 min after which it was heated to RT over 15 min and stirred at RT for 30 min. Saturated aq. NH4Cl (200 mL) was added and the solution was adjusted to pH 1 with 4N HCl (10 mL). The mixture was extracted with EtOAc (×3). The combined organic phases were dried (Na2SO4), filtered and concentrated to afford an oil. The crude product was purified by flash chromatography using heptane:EtOAc 4:1->3:1 as the eluent to afford a crystalline compound which was recrystallised from petroleum ether:Et2O (90:10) to afford the title compound as a crystalline compound.

Workup

  1. additionwas added over 10 min
  2. additionwas added over 10 min
  3. extractionThe mixture was extracted with EtOAc (×3)
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford an oil
  8. customThe crude product was purified by flash chromatography
  9. customEtOAc 4:1->3:1 as the eluent to afford a crystalline compound which
  10. customwas recrystallised from petroleum ether:Et2O (90:10)

Sources & evidence

ORD record
ord-2f2cc13d562c406ba52cc4457096a3bb
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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