Pyridine → 1-Bromo-7-ethyl-3-methylnona-2,6-diene

HRID 1414819Notes

Reaction equation

HRID 1414819 reaction equation
[CH2:1]([C:3]([CH2:12][CH3:13])=[CH:4][CH2:5][CH2:6][C:7]([CH3:11])(O)[CH:8]=[CH2:9])[CH3:2].N1C=CC=CC=1.P(Br)(Br)[Br:21]>CCCCCC>[Br:21][CH2:9][CH:8]=[C:7]([CH3:11])[CH2:6][CH2:5][CH:4]=[C:3]([CH2:12][CH3:13])[CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 214851397-Ethyl-3-methylnona-1,6-dien-3-ol

Product 1

HCID 540586431-Bromo-7-ethyl-3-methylnona-2,6-diene

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

18.2 g. of 7-ethyl-3-methyl-1,6-nonadien-3-ol, 100 ml. of hexane and 1 ml. of anhydrous pyridine are cooled to -15° C. and treated dropwise in the course of 1.5 hours with a solution of 4 ml. of phosphorus tribromide in 50 ml. of hexane, the temperature being maintained at between -15° C. and -10° C. The mixture is stirred for a further 1.5 hours during which time it is allowed to warm up to room temperature slowly. For working up, the mixture is poured onto 50 ml. of ice-water, the organic phase separated and washed in turn with 20 ml. of 10% by weight aqueous sodium carbonate solution, 50 ml. of semi-saturated aqueous sodium chloride solution and 50 ml. of saturated aqueous sodium chloride solution, dried over sodium sulfate and evaporated under reduced pressure. There is obtained 1-bromo-7-ethyl-3-methyl-2,6-nonadiene which is used in the process without further purification.

Workup

  1. additiontreated dropwise in the course of 1.5 hours with a solution of 4 ml
  2. additionthe mixture is poured onto 50 ml
  3. customof ice-water, the organic phase separated
  4. washwashed in turn with 20 ml
  5. dry with materialof saturated aqueous sodium chloride solution, dried over sodium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-77919392f5004574972f6906392c16d4
Source dataset
uspto-grants-1977_01
Patent number
US04002647

Reaction notes

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