Sulfuric Acid → 3-Bromo-5-nitrophenol

HRID 418562노트

반응식

HRID 418562 반응식
N[C:2]1[C:7]([Br:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12].S(=O)(=O)(O)O.N([O-])=O.[Na+]>CCO>[Br:8][C:7]1[CH:2]=[C:3]([OH:12])[CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[CH:6]=1

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 23668193Sodium NitriteHCID 49766558HCID 49766558, 화합물

생성물 1

HCID 104889843-Bromo-5-nitrophenol수율 85.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Compound 98 (33.0 g, 0.14 mol) was treated with sulfuric acid (13.7 mL) and was refluxed in EtOH (550 mL) for 0.5 hours, followed by addition of NaNO2 (23.8 g, 0.35 mol). The resulting mixture was refluxed for additional 1 hour and the volatile was evaporated. The residue was taken up with ethyl acetate and water. The layers were separated and the organic layer was washed with water, saturated sodium bicarbonate, and brine. After removal of solvent, the residue was purified by column chromatography on silica gel to afford the title compound (26 g, 85%); 1H NMR (500 MHz, CD3OD): δ 5.00 (brs, 1H), 7.58 (dd, 1H, J=1.7, 2.3 Hz), 7.47 (t, 1H, J=2.1 Hz), 7.69 (t, 1H, J=1.9 Hz); 13C NMR (125 MHz, CD3OD): δ 110.5, 118.1, 123.7, 125.6, 151.0, 160.5; HRMS (FAB) calcd for C6H4BrNO3(M+) 216.9375. found 216.9374.

후처리

  1. temperatureThe resulting mixture was refluxed for additional 1 hour
  2. customthe volatile was evaporated
  3. customThe layers were separated
  4. washthe organic layer was washed with water, saturated sodium bicarbonate, and brine
  5. customAfter removal of solvent
  6. customthe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-633b8db969a74794b319d60e924d80ec
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093287B2

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