Sulfuric Acid → 3-Bromo-5-nitrophenol

HRID 418562ノート

反応式

HRID 418562 の反応式
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

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 23668193Sodium NitriteHCID 49766558HCID 49766558、化合物

生成物 1

HCID 104889843-Bromo-5-nitrophenol収率 85.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-633b8db969a74794b319d60e924d80ec
出典データセット
uspto-grants-2012_01
特許番号
US08093287B2

反応ノート

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