Benzyl Bromide → 2-(benzyloxy)-4-nitroaniline

HRID 1814293노트

반응식

HRID 1814293 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].CC(C)([O-])C.[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1>[CH2:18]([O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[NH2:1])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 49847212-Amino-5-NitrophenolHCID 23665647Potassium tert-butoxide

생성물 1

HCID 27757972-(benzyloxy)-4-nitroaniline

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The starting 2-amino-5-nitrophenol (21.2 g, 0.14 mol) was dissolved in 350 mL THF. Solid potassium t-butoxide (15.85 g, 0.141 mol) was added slowly, with vigorous stirring. Then a solution of benzylbromide (in 150 mL THF) was added slowly and stirred at room temperature for 2 days. The solvent was removed and the crude oil poured into water (ca. 500 mL) and 3:1 ethyl acetate/methylene chloride (ca. 200 mL). The solid precipitate was filtered off and dried, then recrystallized in toluene to give 2-benzyloxy-4-nitro-phenylamine (9.1 g). The aqueous and organic layers were separated and the aqueous layer was extracted twice with 3:1 ethyl acetate/methylene chloride. The combined organic layers were washed with 5% sodium hydroxide (which formed three layers, and the middle layer contained the desired material by TLC), then the desired layer was washed twice with water, then brine, and dried over anhydrous magnesium sulfate, filtered and the solvent removed. The solid was recrystallized in toluene, filtered and dried to yield 12 g of 2-benzyloxy-4-nitro-phenylamine. (The total yield was 62%.). 1H NMR (CDCl3) 7.9-7.7 (m, 2H), 7.5-7.3 (m, 5H), 6.65 (d, 1H, J=8.68 Hz), 5.15 (s, 2H), 4.57 (br, 2H).

후처리

  1. customThe solvent was removed
  2. additionthe crude oil poured into water (ca. 500 mL) and 3:1 ethyl acetate/methylene chloride (ca. 200 mL)
  3. filtrationThe solid precipitate was filtered off
  4. customdried
  5. customrecrystallized in toluene

출처 및 근거

ORD 기록
ord-ea240b153aed44f08b932efa78150adc
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06875765B2

반응 노트

불러오는 중…