Triphenylphosphine → [4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromide

HRID 5052

반응식

HRID 5052 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][Br:12])=[CH:7][CH:6]=1)=[O:4].[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[Br-:12].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][P+:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:7][CH:6]=1)([O:2][CH3:1])=[O:4]

참가 물질

4

반응물 2

HCID 11776TriphenylphosphineHCID 256687Methyl 4-(bromomethyl)benzoate

생성물 1

HCID 2764257[4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromide수율 90.9%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

To a 2 L 3-neck round bottom flask fitted with a glass stopper, rubber septum, and reflux condenser with a nitrogen inlet tube, was added 64.90 g (283 mmol) methyl 4-bromomethyl benzoate, 81.74 g (311 mmol) triphenylphosphine, and 744 mL toluene. The solution was heated at 80° C. for 5 h. After cooling to room temperature, the reaction vessel was placed in an ice bath. The resulting precipitate was filtered, washed with toluene, and dried in a vacuum oven to afford 126.35 g (89%) (4-carbomethoxy)benzyltriphenylphosphonium bromide as a white solid, mp.=248°-250° C.: 1H NMR (CDCl3, 200 MHz) d 3.86 (s, 3H), 5.70 (d, J=15.3 HZ, 2H), 7.24 (m, 4H), 7.71 (m, 15H).

후처리

  1. customTo a 2 L 3-neck round bottom flask fitted with a glass stopper, rubber septum
  2. temperaturereflux condenser with a nitrogen inlet tube
  3. temperatureAfter cooling to room temperature
  4. customthe reaction vessel was placed in an ice bath
  5. filtrationThe resulting precipitate was filtered
  6. washwashed with toluene
  7. customdried in a vacuum oven

출처 및 근거

ORD 기록
ord-53a7d6a899654a0bba76c803935dd95c
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05243021

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