Sulfuric Acid → 1-Bromo-5-fluoro-2-iodo-3-nitrobenzene

HRID 129849

反応式

HRID 129849 の反応式
[F:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:5](N)=[C:4]([Br:12])[CH:3]=1.S(=O)(=O)(O)O.N([O-])=O.[Na+].[I-:22].[K+]>O.C(OCC)(=O)C>[I:22][C:5]1[C:4]([Br:12])=[CH:3][C:2]([F:1])=[CH:8][C:7]=1[N+:9]([O-:11])=[O:10]

参加物

7

反応物 4

HCID 1118Sulfuric AcidHCID 4875Potassium IodideHCID 2920042-Bromo-4-fluoro-6-nitroanilineHCID 23668193Sodium Nitrite

生成物 1

HCID 194297701-Bromo-5-fluoro-2-iodo-3-nitrobenzene収率 78%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Mix 4-fluoro-2-bromo-6-nitroaniline (15.5 g, 66.0 mmol) and 50% sulfuric acid (200 mL) and cool to 0°-5° C. Add, by dropwise addition, a solution of sodium nitrite (6.0 g, 86.4 mmol) in water (50 mL). Stir for 30 minutes and add solid potassium iodide (29 g, 173 mmol). Take up the product in ethyl acetate (300 mL), wash with saturated sodium hydrogen carbonate (2×200 mL), saturated sodium metabisulfite (2×200 mL) and water (200 mL). Dry (MgSO4), evaporate the solvent in vacuo and purify by silica gel chromatography to give 1-iodo-2-nitro-4-fluoro-6-bromobenzene as a yellow crystalline solid (17.81 g, 76%); mp 75°-76° C.

後処理

  1. temperaturecool to 0°-5° C
  2. additionAdd, by dropwise addition
  3. washwash with saturated sodium hydrogen carbonate (2×200 mL), saturated sodium metabisulfite (2×200 mL) and water (200 mL)
  4. dry with materialDry (MgSO4)
  5. customevaporate the solvent in vacuo
  6. custompurify by silica gel chromatography

出典と根拠

ORDレコード
ord-e00b9406d4074e0cac57050d5114371d
出典データセット
uspto-grants-1995_11
特許番号
US05470870

関連ノート

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