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

HRID 5052

反応式

HRID 5052 の反応式
[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]

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 90.9%

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-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).

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. 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

出典と根拠

ORDレコード
ord-53a7d6a899654a0bba76c803935dd95c
出典データセット
uspto-grants-1993_09
特許番号
US05243021

関連ノート

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