Chlorodiphenylphosphine → (3,4,5-Trimethoxyphenyl)diphenylphosphine

HRID 23863

반응식

HRID 23863 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5](Br)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[Li]CCCC.[P:19](Cl)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([P:19]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]

참가 물질

5

반응물 3

HCID 66180ChlorodiphenylphosphineHCID 758855-Bromo-1,2,3-trimethoxybenzeneHCID 178418339Butyllithium

생성물 1

HCID 14686581(3,4,5-Trimethoxyphenyl)diphenylphosphine수율 80%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 3,4,5-trimethoxybromobenzene 18 (62.3 g, 0.25 mol) in dry THF (200 ml) was added BuLi solution (169 ml, 1.6M in hexane, 0.27 mol) dropwise at −78° C. within 45 min. The resulting beige-colored suspension was stirred for an additional 1 h at −78° C. Then PPh2Cl (61 g, 0.277 mol. 49.7 ml) was added dropwise. The addition was complete within 2 h. The resulting yellow solution was allowed to warm to 0° C. within 2 h and quenched by addition of NH4Cl solution (200 ml). The organic layer was separated, washed with brine (250 ml), dried (Na2SO4), filtered, and evaporated. The solid was recrystallized from methanol to give 69.5 g (80%) of 19.

후처리

  1. additionThe addition
  2. waitwas complete within 2 h
  3. temperatureto warm to 0° C. within 2 h
  4. customquenched by addition of NH4Cl solution (200 ml)
  5. customThe organic layer was separated
  6. washwashed with brine (250 ml)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe solid was recrystallized from methanol

출처 및 근거

ORD 기록
ord-33cdc04604e04380b23741afea793e55
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855657B2

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