Water → 1-Bromo-4-(pentyloxy)benzene

HRID 1938145Notes

Reaction equation

HRID 1938145 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].BrC1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10]N=1.[CH2:15]([O:17][CH2:18][CH3:19])[CH3:16].O.[CH3:21][CH2:22][CH2:23]CC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:14][C:11]1[CH:12]=[CH:13][C:15]([O:17][CH2:18][CH2:19][CH2:21][CH2:22][CH3:23])=[CH:16][CH:10]=1

Participants

7

Reactant 5

HCID 962WaterHCID 3283Diethyl EtherHCID 8003PentaneHCID 10340Sodium CarbonateHCID 693532,5-Dibromopyridine

Product 1

HCID 70169051-Bromo-4-(pentyloxy)benzene

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

To a solution of 1.44 g (6.92 mmol) of a subtitled compound of Preparation 2B in 50 ml of toluene and 20 ml of methanol under nitrogen, was added 15.5 ml (31.1 mmol) a 2M sol. of sodium carbonate which resulted in the formation of a white precipitate. To the resultant mixture, was added 800 mg (0.69 mmol) of palladium tetrakis (triphenylphosphine), followed by 1.64 g (6.92 mmol) of 2,5-dibromopyridine. The resultant reaction mixture was reacted for approximately three hours, forty-five minutes at reflux temperature. When the reaction was substantially complete, as indicated by TLC, the mixture was cooled to room temperature and allowed to stir overnight. The reaction mixture was placed in a separatory funnel and combined with diethyl ether and water. The resultant layers were separated and the organic layer was dried over sodium sulfate, filtered and then concentrated in vacuo to provide a residue. This residue was redissolved in pentane and filtered to provide 0.95 g of the desired compound. The filtrate was recrystallized to provide an additional 1.4 g of the desired compound. These solids were combined and used without further purification. ##STR20##

Workup

  1. customresulted in the formation of a white precipitate
  2. customThe resultant reaction mixture
  3. customwas reacted for approximately three hours, forty-five minutes
  4. temperatureat reflux temperature
  5. customThe reaction mixture was placed in a separatory funnel
  6. customThe resultant layers were separated
  7. dry with materialthe organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto provide a residue
  11. filtrationfiltered

Sources & evidence

ORD record
ord-10eadefe04374bac9be7508e13e335a6
Source dataset
uspto-grants-1997_12
Patent number
US05693611

Reaction notes

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