Tetrahydrofuran → 1-Bromo-4-[1-(2-methoxyvinyl)phenyl]naphthalene

HRID 1890207Notes

Reaction equation

HRID 1890207 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2C=O)=[CH:4][CH:3]=1.[Cl-].COC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[O:43]1[CH2:47]C[CH2:45][CH2:44]1.CC(C)([O-])C.[K+]>O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2([CH:45]=[CH:44][O:43][CH3:47])[CH:17]=[CH:16][CH:15]=[CH:14][CH2:13]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxideHCID 596227241-Bromo-4-(2-formylphenyl)naphthalene

Product 1

HCID 684333991-Bromo-4-[1-(2-methoxyvinyl)phenyl]naphthaleneYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under an argon atmosphere, 170 g of the resulting 1-bromo-4-(2-formylphenyl)naphthalene, 207 g of methoxymethyl triphenylphosphonium chloride and 2.0 L of tetrahydrofuran (THF) were placed in a flask. During stirring at room temperature, 73.6 g of potassium t-butoxide was added to the flask. After further stirring at room temperature for 2 hours, 1.5 L of water was added. The reaction solution was extracted with diethyl ether. An aqueous phase was removed and an organic phase which had been separated was washed with water and saturated brine, and then dried with magnesium sulfate. After the magnesium sulfate was filtered out, the organic phase was concentrated. The resulting residue was purified by means of silica gel column chromatography, whereby 180 g (yield: 99%) of 1-bromo-4-[1-(2-methoxyvinyl)phenyl]naphthalene was obtained.

Workup

  1. stirringAfter further stirring at room temperature for 2 hours
  2. extractionThe reaction solution was extracted with diethyl ether
  3. customAn aqueous phase was removed
  4. customan organic phase which had been separated
  5. washwas washed with water and saturated brine
  6. dry with materialdried with magnesium sulfate
  7. filtrationAfter the magnesium sulfate was filtered out
  8. concentrationthe organic phase was concentrated
  9. customThe resulting residue was purified by means of silica gel column chromatography

Sources & evidence

ORD record
ord-9477d795eeb94852a07f01342490d6a1
Source dataset
uspto-grants-2013_08
Patent number
US08507106B2

Reaction notes

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