1,3-Dibromopropane → 4-(3-Bromopropoxy)-3-methoxybenzonitrile

HRID 2211492Notes

Reaction equation

HRID 2211492 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:10][CH3:11].C([O-])([O-])=O.[K+].[K+].[Br:18][CH2:19][CH2:20][CH2:21]Br>C(#N)C>[Br:18][CH2:19][CH2:20][CH2:21][O:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:10][CH3:11]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 781354-Hydroxy-3-methoxybenzonitrile

Product 1

HCID 104232304-(3-Bromopropoxy)-3-methoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-hydroxy-3-methoxybenzonitrile (7.5 g, 50 mmoles). K2CO3 (12.5 g), and 1,3-dibromopropane (15 g, 75 mmoles) in acetonitrile (100 ml) was heated at reflux for 3 hours and left standing at room temperature overnight. The solvent of the reaction was removed on a rotary evaporator, and the crude solid was extracted into methylene chloride (500 ml). The insolubles were filtered off. The dichloromethane solution was concentrated and the material was purified on a flash chromatography column (SiO2, 105 g; eluted with 2:3 dichloromethane:hexane, and then with dichloromethane). The desired product thus purified weighed 7.74 g (52%). Recrystallization twice from ethanol gave analytically pure 4-(3-bromopropoxy)-3- methoxybenzonitrile, m.p.=99°-101° C.

Workup

  1. temperatureat reflux for 3 hours
  2. waitleft
  3. customThe solvent of the reaction was removed on a rotary evaporator
  4. extractionthe crude solid was extracted into methylene chloride (500 ml)
  5. filtrationThe insolubles were filtered off
  6. concentrationThe dichloromethane solution was concentrated
  7. customthe material was purified on a flash chromatography column (SiO2, 105 g
  8. washeluted with 2:3 dichloromethane
  9. customThe desired product thus purified
  10. customRecrystallization twice from ethanol

Sources & evidence

ORD record
ord-96d1b19b49e94f18b32fb1333da52fdd
Source dataset
uspto-grants-2006_09
Patent number
USRE039265E1

Reaction notes

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