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

HRID 23863

反応式

HRID 23863 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-33cdc04604e04380b23741afea793e55
出典データセット
uspto-grants-2005_02
特許番号
US06855657B2

関連ノート

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