Pyridine → 1-(4-Bromobutoxy)-3-methylbutane

HRID 2398801Notes

Reaction equation

HRID 2398801 reaction equation
P(Br)(Br)([Br:3])=O.[CH2:6]([O:11][CH2:12][CH2:13][CH2:14][CH2:15]O)[CH2:7][CH:8]([CH3:10])[CH3:9].N1C=CC=CC=1>C(Cl)(Cl)Cl>[Br:3][CH2:15][CH2:14][CH2:13][CH2:12][O:11][CH2:6][CH2:7][CH:8]([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24613Phosphorus oxybromideHCID 137211974-Isopentyloxy butanol

Product 1

HCID 214340651-(4-Bromobutoxy)-3-methylbutane

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

6.1 cc (0.0636 mol) of phosphoric tribromide are added dropwise at 0° over the course of 20 minutes and while stirring, to a solution of 27.5 g (0.172 mol) of 4-isopentyloxy-butanol (production: see Example 15) and 1.36 g (0.0172 mol) of pyridine in 150 cc of absolute chloroform. The cooling bath is removed, the mixture is then heated to 60° for 1 hour and stirred at this temperature for 18 hours. The reaction mixture is poured into ice-cold sodium bicarbonate solution, the chloroform phase is removed in a separating funnel, washed with water and saturated sodium chloride solution, dried over magnesium sulphate and evaporated. The residue is filtered with hexane/ethyl acetate (98:2) on silica gel. The evaporated filtrate is fractionally distilled and pure 1-bromo-4-isopentyloxy-butane is obtained. B.P.: 96°-97°/12 mm Hg.

Workup

  1. customThe cooling bath is removed
  2. temperaturethe mixture is then heated to 60° for 1 hour
  3. additionThe reaction mixture is poured into ice-cold sodium bicarbonate solution
  4. customthe chloroform phase is removed in a separating funnel
  5. washwashed with water and saturated sodium chloride solution
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. filtrationThe residue is filtered with hexane/ethyl acetate (98:2) on silica gel
  9. distillationThe evaporated filtrate is fractionally distilled

Sources & evidence

ORD record
ord-a899934d9d7046d3a4f842925283821b
Source dataset
uspto-grants-1977_05
Patent number
US04025641

Reaction notes

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