Bromide ion → 4-Pentenenitrile

HRID 636264

반응식

HRID 636264 반응식
[C-:1]#[N:2].[Na+].[Br-].[CH:5]1([CH2:8]Br)[CH2:7][CH2:6]1.Br[CH:11]1[CH2:14][CH2:13][CH2:12]1.BrC=CCC.BrCCC=C>O>[CH:5]1([CH2:8][C:1]#[N:2])[CH2:7][CH2:6]1.[C:1]([CH2:12][CH2:13][CH:14]=[CH2:11])#[N:2]

참가 물질

9

반응물 6

HCID 259Bromide ionHCID 8929Sodium CyanideHCID 21241Homoallyl bromideHCID 359451-Bromobut-1-eneHCID 78110BromocyclobutaneHCID 81503Bromomethylcyclopropane2회

생성물 2

HCID 116044-PentenenitrileHCID 643447Cyclopropylacetonitrile

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
45 °C

실험 절차

A flask was equipped with stirrer, reflux condenser, thermometer, and charged with 75 ml of water and 36.8 grams (0.75 mole) sodium cyanide. Stirring was commenced and there was added 8.5 grams of tricapryl(methyl)ammonium chloride (ALIQUAT 336 phase-transfer catalyst) followed by 67.5 grams (0.50 mole) of the bromide product mixture comprising 55.7% cyclopropylmethyl bromide, 37.2% bromocyclobutane, and 7.1% bromobutene. The mixture slowly exothermed to about 50° C. After about 1 hour, heating was commenced so as to maintain the temperature of the mixture at 45° C. After 7 hours, gas chromatographic analysis of the organic phase indicated that cyclopropylmethyl bromide and 4-bromo-1-butene (i.e., bromobutene) were consumed, that cyclobutyl bromide was unchanged, and that cyclopropylacetonitrile and 1-cyano-3-butene were formed. The ratio (area %) of cyclopropylacetonitrile to 1-cyano-3-butene was 88:12. A minute trace (less than 1 area %) of cyanocyclobutane was detected.

후처리

  1. customA flask was equipped with stirrer
  2. temperaturereflux condenser
  3. customslowly exothermed to about 50° C
  4. temperatureheating
  5. waitAfter 7 hours
  6. customwere consumed

출처 및 근거

ORD 기록
ord-988db9ccdd2a4ecd8f7f2c6b747c687f
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06191300B1

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