Water → Cyclopropanecarboxylic acid, 3-(2,2-dibromoethenyl)-2,2-dimethyl-, cyano(3-phenoxyphenyl)methyl ester, (1R-(1alpha(S*),3alpha))-

HRID 1155007Notes

Reaction equation

HRID 1155007 reaction equation
[C-:1]#[N:2].[Na+].O.[O:5]([C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=[O:16])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Br:20][C:21]([Br:31])=[CH:22][CH:23]1[CH:25]([C:26](Cl)=[O:27])[C:24]1([CH3:30])[CH3:29]>O.O1CCCC1.O1CCCC1>[Br:20][C:21]([Br:31])=[CH:22][CH:23]1[CH:25]([C:26]([O:16][CH:15]([C:1]#[N:2])[C:14]2[CH:17]=[CH:18][CH:19]=[C:12]([O:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:13]=2)=[O:27])[C:24]1([CH3:30])[CH3:29]

Participants

7

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 382843-PhenoxybenzaldehydeHCID 129405823-(2,2-Dibromoethenyl)-2,2-dimethylcyclopropane-1-carbonyl chloride

Product 1

HCID 2982Cyclopropanecarboxylic acid, 3-(2,2-dibromoethenyl)-2,2-dimethyl-, cyano(3-phenoxyphenyl)methyl ester, (1R-(1alpha(S*),3alpha))-Yield 115%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Sodium cyanide (0.80 g, 0.016 mole) was charged to a reaction vessel together with 25 ml of a mixture of water and tetrahydrofuran (1/1 by volume). 3-Phenoxybenzaldehyde (2.31 g, 0.012 mole) in 10 ml of water/tetrahydrofuran solution (1/1 by volume) was then added in one portion, and 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarbonyl chloride (4.4 g, 0.014 mole) was added dropwise over a 15 minute period. The reaction mixture was stirred for 2 hours at 20°, and the desired ester (6.97 g, 86% pure by glpc) was isolated as described in Example 1E. EXAMPLE 3

Workup

  1. additionwas added dropwise over a 15 minute period

Sources & evidence

ORD record
ord-653df502c4eb44a2852f90dcf41cff8b
Source dataset
uspto-grants-1981_11
Patent number
US04299776

Reaction notes

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