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

HRID 1196154

反応式

HRID 1196154 の反応式
[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]

参加物

4

反応物 2

HCID 11776TriphenylphosphineHCID 256687Methyl 4-(bromomethyl)benzoate

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-11e01dd97e7e434789ac5027e2e3e89a
出典データセット
uspto-grants-1992_05
特許番号
US05113010

関連ノート

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