3-Methylbenzo[b]thiophene → 2-Fluoro-3-methyl-1-benzothiophene

HRID 10229

反応式

HRID 10229 の反応式
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1.[B-](F)(F)(F)[F:12].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(#N)C>[F:12][C:3]1[S:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:2]=1[CH3:1]

参加物

4

反応物 2

HCID 738173-Methylbenzo[b]thiopheneHCID 2724933Selectfluor

生成物 1

HCID 219783712-Fluoro-3-methyl-1-benzothiophene収率 72%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

A stirred solution of 3-methylbenzothiophene (0.51 g, 3.37 mmol) in acetonitrile (5 μL) under nitrogen was treated with SELECTFLUOR™ (1.25 g, 3.35 mmol) and heated to 70° C. overnight. The solvent was removed in vacuo. The residue was taken up in ethyl acetate and washed with sodium hydrogen carbonate solution, water and brine, dried over MgSO4 and evaporated in vacuo. Purification by flash column chromatography on silica, eluting with isohexane, gave 2-fluoro-3-methyl-1-benzothiophene (72% pure, 190 mg, 0.82 mmol) which was treated according to the method of Example 29 Step 2 to give 3-(bromomethyl)-2-fluoro-1-benzothiophene (95 mg, 12%). 1H NMR (500 MHz, CDCl3) δ 7.75 (1H, d, J=8.0 Hz), 7.68 (1H, d, J=8.0 Hz), 7.46 (1H, t, J=7.6 Hz), 7.39–7.35 (1H, m), 4.65 (2H, s).

後処理

  1. customThe solvent was removed in vacuo
  2. washwashed with sodium hydrogen carbonate solution, water and brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customPurification by flash column chromatography on silica
  6. washeluting with isohexane

出典と根拠

ORDレコード
ord-25fc685f89c34fc6805c7197facceebe
出典データセット
uspto-grants-2006_08
特許番号
US07094777B2

関連ノート

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