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

HRID 10229

반응식

HRID 10229 반응식
[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]

참가 물질

4

반응물 2

HCID 738173-Methylbenzo[b]thiopheneHCID 2724933Selectfluor

생성물 1

HCID 219783712-Fluoro-3-methyl-1-benzothiophene수율 72%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-25fc685f89c34fc6805c7197facceebe
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094777B2

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