Water → HCID 131713017, compound

HRID 2166730Notes

Reaction equation

HRID 2166730 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[CH:11]([OH:14])[C:12]#[N:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:18][C:19]([C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1)([Br:30])[CH:20]([C@H:22]1[C@H:24]([C:25](Cl)=[O:26])[C:23]1([CH3:29])[CH3:28])[Br:21].N1C=CC=CC=1.O>C1(C)C=CC=CC=1>[C:12]([CH:11]([O:14][C:25]([C@H:24]1[C@H:22]([CH:20]([Br:21])[C:19]([Cl:18])([C:31]2[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=2)[Br:30])[C:23]1([CH3:29])[CH3:28])=[O:26])[C:10]1[CH:15]=[CH:16][CH:17]=[C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:9]=1)#[N:13]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 93218Benzeneacetonitrile, alpha-hydroxy-3-phenoxy-, (alphaS)-HCID 131713015HCID 131713015, compound

Product 1

HCID 131713017HCID 131713017, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

2.25 g (0.01 mol) of 3-phenoxy-α-cyanobenzyl alcohol and 4.63 g (0.01 mol) of trans-3-(2-chloro-2-(4-chloro-phenyl)-1,2-dibromoethyl)-2,2-dimethyl-cyclo-propane-1-(R,S)-carboxylic acid chloride were dissolved in 100 ml of anhydrous toluene, and 0.8 g (0.01 mol) of pyridine, dissolved in 200 ml of toluene, was added dropwise at 25°-30° C., while stirring. The reaction mixture was then stirred for a further 3 hours at 25° C. It was poured into 150 ml of water and the organic phase was separated off and washed again with 100 ml of water. The toluene phase was then dried over sodium sulphate and the solvent was distilled off under a waterpump vacuum. Last residues of solvent were removed by brief incipient distillation at a bath temperature of 60° C./1 mm Hg. 6 g (92% of theory) of trans-3-(2-chloro-2-(4-chloro-phenyl)-1,2-dibromoethyl)-2,2-dimethylcyclopropane-1-(R,S)-carboxylic acid α-(R,S)-cyano-3-phenoxy-benzyl ester were obtained as a viscous oil. The structure was confirmed by the 1H-NMR spectrum.

Workup

  1. additionwas added dropwise at 25°-30° C.
  2. stirringThe reaction mixture was then stirred for a further 3 hours at 25° C
  3. customthe organic phase was separated off
  4. washwashed again with 100 ml of water
  5. dry with materialThe toluene phase was then dried over sodium sulphate
  6. distillationthe solvent was distilled off under a waterpump vacuum
  7. customLast residues of solvent were removed by brief incipient distillation at a bath temperature of 60° C./1 mm Hg

Sources & evidence

ORD record
ord-ffdc85a0928b42fbad2d4e6c03a8fa65
Source dataset
uspto-grants-1983_06
Patent number
US04388322

Reaction notes

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