Allyl bromide → HCID 10750085, compound

HRID 1704805Notes

Reaction equation

HRID 1704805 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.C(NC1CCCCC1)(C)C.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]#[N:26])=[CH:20][CH:19]=1.C(Br)C=C>O1CCCC1.C(OCC)C>[CH2:3]([CH:24]([C:21]1[CH:22]=[CH:23][C:18]([O:17][CH3:16])=[CH:19][CH:20]=1)[C:25]#[N:26])[CH:2]=[CH2:1]

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 62386CyclohexylisopropylamineHCID 66031Benzeneacetonitrile, 4-methoxy-HCID 178418339Butyllithium

Product 1

HCID 10750085HCID 10750085, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyl lithium (0.16 mole of 1.6 M in hexane) was added under a nitrogen atmosphere to dry tetrahydrofuran (100 ml.) which was cooled in a CO2 -acetone bath. This was followed by the successive dropwise additions during 10 minutes of solutions in tetrahydrofuran (10 ml. each) of N-isopropylcyclohexylamine (22.6 g., 0.160 mole) and p-methoxyphenylacetonitrile (21.2 g., 0.144 mole). The mixture was stirred in the cold for 10 minutes when allyl bromide (24.2 g., 0.20 mole) was added dropwise during 10 minutes. Stirring was continued in the cold for 15 minutes and then at ambient temperature for 1.5 hours. The solution was diluted with diethyl ether and washed successively with 4% hydrochloric acid (2 × 100 ml.) H2O and brine. The ethereal solution was dried (Na2SO4), concentrated, and the residue distilled to give 24.2 g. (89% yield) of the nitrile, b.p. 99°-114° (0.1 mm.).

Workup

  1. temperaturewas cooled in a CO2 -acetone bath
  2. additionwas added dropwise during 10 minutes
  3. customcold for 15 minutes
  4. washwashed successively with 4% hydrochloric acid (2 × 100 ml.) H2O and brine
  5. dry with materialThe ethereal solution was dried (Na2SO4)
  6. concentrationconcentrated
  7. distillationthe residue distilled
  8. customto give 24.2 g

Sources & evidence

ORD record
ord-00182f9e6d354955bdef9fdca1980f40
Source dataset
uspto-grants-1978_11
Patent number
US04127720

Reaction notes

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