Pyridine → 2,2-Dimethyl-3-(1-bromo-2,2-dichloro-2-bromoethyl)-cyclopropanecarboxylic acid-3-(phenoxy)-alpha-vinyl-benzyl ester

HRID 1155374Notes

Reaction equation

HRID 1155374 reaction equation
N1C=CC=CC=1.[O:7]([C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=1)[CH:17]([OH:20])[CH:18]=[CH2:19])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:24][C:25]1([CH3:37])[CH:27]([CH:28]([Br:33])[C:29]([Cl:32])([Cl:31])[Br:30])[CH:26]1[C:34](Cl)=[O:35]>C1C=CC=CC=1>[O:7]([C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=1)[CH:17]([O:20][C:34]([CH:26]1[CH:27]([CH:28]([Br:33])[C:29]([Cl:31])([Cl:32])[Br:30])[C:25]1([CH3:37])[CH3:24])=[O:35])[CH:18]=[CH2:19])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 128743462,2-Dimethyl-3-(1-bromo-2,2-dichloro-2-bromoethyl)-cyclopropanecarboxylic acid chlorideHCID 129613931-(3-Phenoxyphenyl)prop-2-en-1-ol

Product 1

HCID 205621552,2-Dimethyl-3-(1-bromo-2,2-dichloro-2-bromoethyl)-cyclopropanecarboxylic acid-3-(phenoxy)-alpha-vinyl-benzyl ester

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

3.2 g of pyridine in 10 ml of benzene is added dropwise at 5° C., with stirring, to 8 g of 3-phenoxy-α-vinyl-benzyl alcohol in 30 ml of benzene. After the addition of 14 g of 2,2-dimethyl-3-(1-bromo-2,2-dichloro-2-bromoethyl)-cyclopropanecarboxylic acid chloride at 10° C., the mixture is stirred for 2 hours at room temperature, and is allowed to stand for a further 10 hours at this temperature. The reaction mixture is diluted with ice water; the organic layer is extracted three times with 100ml of 3% HCl each time, and subsequently three times with 100 ml of 3% sodium bicarbonate each time; the organic phase is dried with sodium sulfate, and the benzene is distilled off. There is obtained the compound of the formula ##STR9## as colourless oil having a refractive index of nD40° =1.5776. In an analogous manner is also obtained the compound of the formula ##STR10##

Workup

  1. waitto stand for a further 10 hours at this temperature
  2. extractionthe organic layer is extracted three times with 100ml of 3% HCl each time, and subsequently three times with 100 ml of 3% sodium bicarbonate each time
  3. dry with materialthe organic phase is dried with sodium sulfate
  4. distillationthe benzene is distilled off
  5. customThere is obtained the compound of the formula ##STR9## as colourless oil
  6. customIn an analogous manner is also obtained the compound of the formula

Sources & evidence

ORD record
ord-ece32dfc1fb7474682b79add0b17b982
Source dataset
uspto-grants-1981_11
Patent number
US04301304

Reaction notes

Loading…