Potassium Fluoride → HCID 10407453, compound

HRID 218252Notes

Reaction equation

HRID 218252 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](/[CH:8]=[CH:9]\[C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=2)[C:5]([O:22][Si](C(C)(C)C)(C)C)=[C:4]([O:30][Si](C(C)(C)C)(C)C)[CH:3]=1.[F-].[K+]>CO.CN(C)C=O.C(O)(=O)C.C(OC)(C)(C)C>[Br:1][C:2]1[CH:7]=[C:6](/[CH:8]=[CH:9]\[C:10]2[CH:11]=[C:12]([O:20][CH3:21])[C:13]([O:18][CH3:19])=[C:14]([O:16][CH3:17])[CH:15]=2)[C:5]([OH:22])=[C:4]([OH:30])[CH:3]=1

Participants

6

Reactant 2

HCID 522689Potassium FluorideHCID 601306724-Bromo-6-[(Z)-2-(3,4,5-trimethoxyphenyl)vinyl]-1,2-di(tert-butyldimethylsilyloxy)benzene

Product 1

HCID 10407453HCID 10407453, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 15413tert-Butyl methyl etherSolventHCID 21901440N,N-dimethylformamide methanolSolvent

Procedure

To a solution of 20 (0.19 g, 0.32 mmol) in methanol:dimethylformamide 1:1 (4 mL), acetic acid was added (0.114 mL, 1.9 mmol) followed by potassium fluoride (0.110 mg, 1.9 mmol). The mixture was stirred for 30 hours then diluted with tertbutylmethyl ether (50 mL) and washed with water (20 mL) then brine (20 mL), then dried over sodium sulphate. The solvent was removed under reduced pressure to give a crude which was purified by column (cyclohexane:AcOEt 7:3+1% AcOH) to give 0.097 g of ZSB-74:

Workup

  1. washwashed with water (20 mL)
  2. dry with materialbrine (20 mL), then dried over sodium sulphate
  3. customThe solvent was removed under reduced pressure
  4. customto give a crude which
  5. customwas purified by column (cyclohexane:AcOEt 7:3+1% AcOH)
  6. customto give 0.097 g of ZSB-74

Sources & evidence

ORD record
ord-1893776e350a4ca2bfce44fb5ee61421
Source dataset
uspto-grants-2012_06
Patent number
US08198302B2

Reaction notes

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