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

HRID 1196154

반응식

HRID 1196154 반응식
[Br:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[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-:1].[C:7]([C:6]1[CH:11]=[CH:12][C:3]([CH2:2][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:4][CH:5]=1)([O:9][CH3:10])=[O:8]

참가 물질

4

반응물 2

HCID 11776TriphenylphosphineHCID 256687Methyl 4-(bromomethyl)benzoate

생성물 1

HCID 2764257[4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromide수율 89%

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-bromomethylbenzoate, 81.74 g (311 mmol) triphenylphosphine, and 744 mL toluene. The solution was heated at 80° C. for 5h. After cooling to room temperature, 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. (reported in V. Sankaran and C. S. Marvel, J. Polym. Sci, Poly. Chem. Ed , 17, 3949 (1979) as 258°-260° C.): 1H NMR (CDCl3, 200 MHz) δ 3.86 (s,3H), 5.70 (d,J=15.3 Hz, 2H), 7.24 (m,4H), 7.71 (m, 15 H).

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. customreaction vessel
  5. customwas placed in an ice bath
  6. filtrationThe resulting precipitate was filtered
  7. washwashed with toluene
  8. customdried in a vacuum oven

출처 및 근거

ORD 기록
ord-11e01dd97e7e434789ac5027e2e3e89a
출처 데이터셋
uspto-grants-1992_05
특허 번호
US05113010

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