Pyridine → HCID 21483938, compound

HRID 1415195Notes

Reaction equation

HRID 1415195 reaction equation
P(Br)(Br)[Br:2].N1C=CC=CC=1.[Cl:11][C:12]1[CH:13]=[C:14]([CH2:21][CH2:22][CH2:23]O)[CH:15]=[C:16]([O:19][CH3:20])[C:17]=1[Cl:18]>C1(C)C=CC=CC=1>[Cl:18][C:17]1[C:12]([Cl:11])=[CH:13][C:14]([CH2:21][CH2:22][CH2:23][Br:2])=[CH:15][C:16]=1[O:19][CH3:20]

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 24614Phosphorus tribromideHCID 21483907HCID 21483907, compound

Product 1

HCID 21483938HCID 21483938, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-5 °C

Procedure

In a four-necked flask fitted with a stirrer, internal thermometer, dropping funnel and calcium chloride tube is placed freshly distilled phosphorus tribromide (9.6 g., 0.036 mole) and dry toluene (50 ml.). To this is added dry pyridine (1.5 g.). The mixture is stirred for 15 minutes and then cooled to -5° C. A mixture of the product of Step 2 (23.5 g., 0.1 mole) and pyridine (0.5 g.) in toluene (50 ml.) is added dropwise with stirring at -5° C. to -3° C. over a one hour period. The reaction mixture is stirred at -5° C. to -3° C. for an additional hour and then allowed to warm up to 20°-25° C. The mixture is kept for 48 hours and then added to ice water (ca. 500 ml.). The toluene layer is separated and washed with water, dilute hydrochloric acid, sodium bicarbonate solution and again with water. After drying over Na2SO4 and evaporation of the toluene under reduced pressure there is obtained 2,3-dichloro-5-(3-bromopropyl)anisole.

Workup

  1. customIn a four-necked flask fitted with a stirrer
  2. additionis added dropwise
  3. stirringwith stirring at -5° C. to -3° C. over a one hour period
  4. stirringThe reaction mixture is stirred at -5° C. to -3° C. for an additional hour
  5. temperatureto warm up to 20°-25° C
  6. waitThe mixture is kept for 48 hours
  7. customThe toluene layer is separated
  8. washwashed with water, dilute hydrochloric acid, sodium bicarbonate solution and again with water
  9. dry with materialAfter drying over Na2SO4 and evaporation of the toluene under reduced pressure

Sources & evidence

ORD record
ord-7060c575f1fb440381a35587dfdd1b3f
Source dataset
uspto-grants-1977_01
Patent number
US04003927

Reaction notes

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