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

HRID 223767

반응식

HRID 223767 반응식
[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]

참가 물질

4

반응물 2

HCID 11776TriphenylphosphineHCID 517981Methyl 3-(bromomethyl)benzoate

생성물 1

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

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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%.

후처리

  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)

출처 및 근거

ORD 기록
ord-987b5be7905646a38caa4a2b0300121a
출처 데이터셋
uspto-grants-1982_10
특허 번호
US04356292

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