Water → HCID 13091948, compound

HRID 1284970Notes

Reaction equation

HRID 1284970 reaction equation
S(C1C=CC(C)=CC=1)(O[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])(=O)=O.CN(P(N(C)C)(N(C)C)=O)C.[Br-:31].[K+].O>C1COCC1.C1OCCOCCOCCOCCOCCOC1>[CH3:11][C:10]([CH3:12])=[CH:9][CH2:8][CH2:7][CH2:6][CH2:5][Br:31]

Participants

7

Reactant 4

HCID 962WaterHCID 12679HexamethylphosphoramideHCID 253877Potassium BromideHCID 13091947HCID 13091947, compound

Product 1

HCID 13091948HCID 13091948, compoundYield 76.6%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 11 g of 6-methyl-5-heptenyl tosylate in 100 ml of THF were added 10 ml of HMPA, 50 g of potassium bromide and 300 mg of 18-crown-6, and the resulting mixture was refluxed for 5 hours. After cooling, water was added, and the mixture was concentrated, the residue was extracted with pentane 3 times, the combined organic layers were washed with a saturated aqueous solution of sodium hydrogen carbonate water and saturated brine, dried and concentrated to give 8 g of an oily substance. This oily substance was distilled (bp 70° C./5 mm Hg) to yield 5.7 g of a pure bromide.

Workup

  1. temperaturethe resulting mixture was refluxed for 5 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated
  4. extractionthe residue was extracted with pentane 3 times
  5. washthe combined organic layers were washed with a saturated aqueous solution of sodium hydrogen carbonate water and saturated brine
  6. customdried
  7. concentrationconcentrated
  8. customto give 8 g of an oily substance
  9. distillationThis oily substance was distilled (bp 70° C./5 mm Hg)

Sources & evidence

ORD record
ord-c1258102ce01404095765d37d5a4f794
Source dataset
uspto-grants-1986_01
Patent number
US04564620

Reaction notes

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