5-Bromo-1,2,3-trimethoxybenzene → HCID 86589618, compound

HRID 1723915Notes

Reaction equation

HRID 1723915 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([O:10][CH3:11])=[C:6]([O:8][CH3:9])[CH:7]=1.C([Li])(C)(C)C.[CH3:19][C:20]12[CH:29]([CH:30]=[O:31])[CH2:28][CH2:27][CH:26]=[C:25]1[CH2:24][C:23]1([S:35][CH2:34][CH2:33][S:32]1)[CH2:22][CH2:21]2>CCOCC>[CH3:19][C:20]12[CH:29]([CH:30]([C:2]3[CH:3]=[C:4]([O:12][CH3:13])[C:5]([O:10][CH3:11])=[C:6]([O:8][CH3:9])[CH:7]=3)[OH:31])[CH2:28][CH2:27][CH:26]=[C:25]1[CH2:24][C:23]1([S:32][CH2:33][CH2:34][S:35]1)[CH2:22][CH2:21]2

Participants

5

Reactant 3

HCID 758855-Bromo-1,2,3-trimethoxybenzeneHCID 86589619HCID 86589619, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 86589618HCID 86589618, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution 5-bromo-1,2,3-trimethoxy-benzene (276 mg, 1.12 mmol) dissolved in 6 mL anhydrous ether is cooled to −78° C. and tert-butyllithium (1.7 M in pentane, 1.32 mL, 2.24 mmol) is added. The mixture was stirred at −78° C. for 15 minutes, then at room temperature for 3 hours. Aldehyde 241 (100 mg, 0.373 mmol) was added dropwise over 10 minutes in 10 mL ether at −30° C. The mixture was stirred for 0.5 hours and the reaction quenched with dropwise addition of saturated aqueous NH4+Cl−. The phases were separated and the aqueous phase was extracted with ether (4×10 mL). The pooled organic extracts were washed with saturated aqueous NaHCO3, brine, dried (MgSO4), filtered and concentrated under vacuum. The residue was purified by flash chromatography over silica gel (25% ethyl acetate-hexanes) to yield 243(119 mg, 73%).

Workup

  1. waitat room temperature for 3 hours
  2. stirringThe mixture was stirred for 0.5 hours
  3. customthe reaction quenched with dropwise addition of saturated aqueous NH4+Cl−
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with ether (4×10 mL)
  6. washThe pooled organic extracts were washed with saturated aqueous NaHCO3, brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe residue was purified by flash chromatography over silica gel (25% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-65efa050da80417a996faae23cd72a2c
Source dataset
uspto-grants-2009_02
Patent number
US07485660B2

Reaction notes

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