Phosphorus tribromide → 2-Bromomethyl-anthraquinone

HRID 266031노트

반응식

HRID 266031 반응식
P(Br)(Br)[Br:2].O[CH2:6][C:7]1[CH:20]=[CH:19][C:18]2[C:17](=[O:21])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:22])[C:9]=2[CH:8]=1>O1CCCC1>[Br:2][CH2:6][C:7]1[CH:20]=[CH:19][C:18]2[C:17](=[O:21])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:22])[C:9]=2[CH:8]=1

참가 물질

4

반응물 2

HCID 24614Phosphorus tribromideHCID 870142-(Hydroxymethyl)anthraquinone

생성물 1

HCID 3444522-Bromomethyl-anthraquinone수율 52%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of PBr3 (82 mg, 302 μmole) in 5 mL of tetrahydrofuran (THF) was placed in ice bath. 2-Hydroxymethylanthraquinone (100 mg, 421 μmole) obtained from Aldrich Chemical Co., St. Louis, Miss., in 10 mL of THF was added to the mixture slowly over 10 minutes. After 1 hour at 0° C., the reaction temperature was raised to room temperature and the mixture was stirred for 48 hours. The mixture was evaporated and then redissolved in ethyl acetate for H2O extraction. The organic layer was dried over MgSO4 and filtered, and the solvent was removed under reduced pressure. 2-Bromomethylanthraquinone was purified by flash silica column chromatography (Yield=52%). 1H NMR (300 MHz, CDCl3) δ 8.24 (2H, m), 8.14 (1H, s), 8.01(1H,d), 7.70 (1H, d), 7.57 (2H, m), 4.68 (2H, s).

후처리

  1. customThe mixture was evaporated
  2. dissolutionredissolved in ethyl acetate for H2O extraction
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. custom2-Bromomethylanthraquinone was purified by flash silica column chromatography (Yield=52%)

출처 및 근거

ORD 기록
ord-dbf38bf8d71d4307a1ff9f46b056bea1
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05650399

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