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

HRID 1722333노트

반응식

HRID 1722333 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 8021Diethylamine용매

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-faa30264305d4ebdb1c8ba56d797c0bf
출처 데이터셋
uspto-grants-1989_08
특허 번호
US04855324

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