5-Bromo-1,2,3-trimethoxybenzene → HCID 19754873, compound

HRID 1588932Notes

Reaction equation

HRID 1588932 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](Br)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[Li]CCCC.[CH:19]([N:22]([CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)[C:23](=[O:34])[C:24]1[CH:29]=[CH:28][C:27]([CH:30]=[O:31])=[C:26]([O:32][CH3:33])[CH:25]=1)([CH3:21])[CH3:20].OS([O-])(=O)=O.[K+]>C(OCC)C.C1COCC1>[CH:35]1([N:22]([CH:19]([CH3:21])[CH3:20])[C:23](=[O:34])[C:24]2[CH:29]=[CH:28][C:27]([CH:30]([OH:31])[C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=3)=[C:26]([O:32][CH3:33])[CH:25]=2)[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]1

Participants

7

Reactant 4

HCID 758855-Bromo-1,2,3-trimethoxybenzeneHCID 516920Potassium bisulfateHCID 10425081HCID 10425081, compoundHCID 178418339Butyllithium

Product 1

HCID 19754873HCID 19754873, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-8 °C

Procedure

To a stirred, cold (-15°) solution of 3,4,5-trimethoxybromobenzene (965 mg, 3.9 mmol) in ethyl ether (15 ml) is added n-BuLi (3 ml of 1.6 M solution in hexane). The reaction mixture is stirred at -8° C. for 10 min., diluted with THF (5 ml) and warmed to 0° C. After stirring for 5 min., the reaction is cooled to -30° C. and a solution of 4-formyl-3-methoxybenzoic acid N-isopropyl-N-cyclohexyl amide (1.18 g, 3.9 mmol) in THF (5 ml) is added. After stirring at -30° C. for 10 min. and warming to room temperature, the reaction is poured onto 0.5 N KHSO4 and extracted with ethyl acetate. The organic layer is washed with saturated NaCl solution and dried (MgSO4). The drying agent is filtered and the filtrate concentrated in vacuo to give the crude product. This is chromatographed on silica gel using mixtures of ethyl acetate and hexane as eluents to give the title compound.

Workup

  1. temperaturewarmed to 0° C
  2. stirringAfter stirring for 5 min.
  3. temperaturethe reaction is cooled to -30° C.
  4. stirringAfter stirring at -30° C. for 10 min.
  5. temperaturewarming to room temperature
  6. extractionextracted with ethyl acetate
  7. washThe organic layer is washed with saturated NaCl solution
  8. dry with materialdried (MgSO4)
  9. filtrationThe drying agent is filtered
  10. concentrationthe filtrate concentrated in vacuo
  11. customto give the crude product
  12. customThis is chromatographed on silica gel using mixtures of ethyl acetate and hexane as eluents

Sources & evidence

ORD record
ord-c853ff96a63640ecbc9edd666f849d76
Source dataset
uspto-grants-1993_06
Patent number
US05223539

Reaction notes

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