Triphenylphosphine → 3-(3-Bromopropoxy)benzonitrile

HRID 366451Notes

Reaction equation

HRID 366451 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1)#[N:2].[Br:10][CH2:11][CH2:12][CH2:13]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.CCOCC>[Br:10][CH2:11][CH2:12][CH2:13][O:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[C:1]#[N:2]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 123083-Bromo-1-propanolHCID 133943-CyanophenolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 102433503-(3-Bromopropoxy)benzonitrile

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Cyanophenol (10.0 g, 84 mM), 3-bromopropanol (20.3 mL, 114 mM), triphenylphosphine (29.7 g, 114 mM) were stirred in anhydrous THF (40 mL) at room temperature and treated with diethylazodicarboxylate (17.8 mL, 114 mM) dropwise over 5 min. under an atmosphere of nitrogen. This mixture stirred for about 5 hours then diluted with ether (500 mL) and filtered through Celite™. The filtrate was concentrated to a reddish oil which was again dissolved in ether (250 mL), diluted with hexanes (200 mL) and filtered. The filtrates were concentrated then filtered through a silica pad (300 g) eluting with 35% acetone/hexanes to collect the desired product as a yellow oil, 16.85 g. This material was used in its crude form.

Workup

  1. filtrationfiltered through Celite™
  2. concentrationThe filtrate was concentrated to a reddish oil which
  3. dissolutionwas again dissolved in ether (250 mL)
  4. additiondiluted with hexanes (200 mL)
  5. filtrationfiltered
  6. concentrationThe filtrates were concentrated
  7. filtrationthen filtered through a silica pad (300 g)
  8. washeluting with 35% acetone/hexanes
  9. customto collect the desired product as a yellow oil, 16.85 g

Sources & evidence

ORD record
ord-7b16a01611e84f738fc7e17009ef6e43
Source dataset
uspto-grants-2000_10
Patent number
US06130217

Reaction notes

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