Triphenylphosphine → Phosphonium, [[3-(methoxycarbonyl)phenyl]methyl]triphenyl-, bromide

HRID 223767

反応式

HRID 223767 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH2:11][Br:12])[CH:8]=[CH:9][CH:10]=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>C1C=CC=CC=1>[Br-:12].[C:3]([C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[CH2:11][P+:19]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)([O:2][CH3:1])=[O:4]

参加物

4

反応物 2

HCID 11776TriphenylphosphineHCID 517981Methyl 3-(bromomethyl)benzoate

生成物 1

HCID 10051285Phosphonium, [[3-(methoxycarbonyl)phenyl]methyl]triphenyl-, bromide

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

A mixture of 230 g (1.0 mole) of methyl-α-bromo-m-toluate and 300 g (1.2 mole) of triphenyl phosphine in 1 l of dry benzene was refluxed for 2 hr. After 15 minutes, the phosphonium bromide started precipitating from the solution. After cooling the flask to room temperature, the solid was filtered, washed with plenty of petroleum ether and dried. The yield 487 g was quantitative. m.p. 234°-236° C. The infrared spectrum showed absorption of 1720 cm-1 (COOCH3). NMR (CDCl3) showed 3.8 (S, --COOCH3, 3), 5.5-5.8 (d, --CH2 -P, 2), and 7-8.4 (m, aromatic, 19). Anal. calcd. for C27H24O2P Br: C, 65.98%, H, 4.88%, Br. 16.29%. Found: C, 65.88%, H, 4.82%, Br, 16.49%.

後処理

  1. temperaturewas refluxed for 2 hr
  2. customthe phosphonium bromide started precipitating from the solution
  3. filtrationthe solid was filtered
  4. washwashed with plenty of petroleum ether
  5. customdried
  6. customabsorption of 1720 cm-1 (COOCH3)

出典と根拠

ORDレコード
ord-987b5be7905646a38caa4a2b0300121a
出典データセット
uspto-grants-1982_10
特許番号
US04356292

関連ノート

読み込み中…