Hydrochloric Acid → 5-(2-Bromophenyl)-4-pentynoic acid

HRID 1722333ノート

反応式

HRID 1722333 の反応式
[C:1]([OH:7])(=[O:6])[CH2:2][CH2:3][C:4]#[CH:5].[Br:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1I.Cl>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].[Cu]I.C(NCC)C>[Br:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:5]#[C:4][CH2:3][CH2:2][C:1]([OH:7])=[O:6]

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 114151-Bromo-2-iodobenzeneHCID 224644-Pentynoic acid

生成物 1

HCID 147984675-(2-Bromophenyl)-4-pentynoic acid

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 8021Diethylamine溶媒

実験手順

To 10 ml of diethylamine was added with stirring 0.5 g (5.1 mmol) of 4-pentynoic acid, 1.4g (5 mmol) of 1-bromo-2-iodobenzene, and 60mg (0.05 mmol) of tetrakis(triphenylphosphine)palladium(O) The slurry was degassed with argon and 0.19g (1.0 mmol) of CuI was added. The reaction mixture was stirred for 2 hr. at room temperature and then poured into approximately 100ml of a 10% HCl solution. The resulting precipitate was filtered, washed with water and dried. The solid was taken up in hot CHCl3 and filtered to remove insoluble salts. After evaporation of the solvent, the resulting orange solid was recrystallized from a chloroform-hexane mixture to produce a tan solid, m.p. 87-91°C.

後処理

  1. additionwas added
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. customdried
  5. filtrationfiltered
  6. customto remove insoluble salts
  7. customAfter evaporation of the solvent
  8. customthe resulting orange solid was recrystallized from a chloroform-hexane mixture
  9. customto produce a tan solid, m.p. 87-91°C.

出典と根拠

ORDレコード
ord-faa30264305d4ebdb1c8ba56d797c0bf
出典データセット
uspto-grants-1989_08
特許番号
US04855324

反応ノート

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