N-Bromosuccinamide → 5-(5-Bromooxazol-2-yl)-2-isopropoxybenzonitrile

HRID 1053753ノート

反応式

HRID 1053753 の反応式
[O:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[CH:7]=[CH:8][C:9]([O:14][CH:15]([CH3:17])[CH3:16])=[C:10]([CH:13]=1)[C:11]#[N:12].[Br:18]NC(=O)CCC(N)=O>C(Cl)(Cl)(Cl)Cl>[Br:18][C:5]1[O:1][C:2]([C:6]2[CH:7]=[CH:8][C:9]([O:14][CH:15]([CH3:17])[CH3:16])=[C:10]([CH:13]=2)[C:11]#[N:12])=[N:3][CH:4]=1

参加物

4

反応物 2

HCID 9834204N-BromosuccinamideHCID 583549695-(4,5-Dihydrooxazol-2-yl)-2-isopropoxybenzonitrile

生成物 1

HCID 583549795-(5-Bromooxazol-2-yl)-2-isopropoxybenzonitrile収率 55%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

A stirring solution of 5-(4,5-dihydrooxazol-2-yl)-2-isopropoxybenzonitrile INT-31 (420 mg, 1.82 mmol), N-bromosuccinamide (990 mg, 5.56 mmol) and azoisobutyronitrile (14.9 mg, 0.09 mmol) in carbon tetrachloride (20 mL) was heated at 80° C. under N2 for 18 h. The reaction mixture was cooled to room temperature and the solids were removed by filtration. The filtrate was washed with sodium thiosulfate (20 mL) and brine (20 mL), and dried over MgSO4. The product was purified by chromatography (EA/hexanes) to afford 300 mg (55%) of 5-(5-bromooxazol-2-yl)-2-isopropoxybenzonitrile INT-32 as a yellow solid. LCMS-ESI (m/z) calculated for C13H11BrN2O2: 307.1; found 309.0 [M+2]+, tR=3.79 min. 1H NMR (400 MHz, CDCl3) δ 8.19-7.93 (m, 2H), 7.08-6.85 (m, 2H), 4.81-4.47 (m, 1H), 1.38 (dd, J=6.6, 3.0 Hz, 6H).

後処理

  1. customthe solids were removed by filtration
  2. washThe filtrate was washed with sodium thiosulfate (20 mL) and brine (20 mL)
  3. dry with materialdried over MgSO4
  4. customThe product was purified by chromatography (EA/hexanes)

出典と根拠

ORDレコード
ord-5f21065e01934674a7d880859dc53e39
出典データセット
uspto-grants-2016_07
特許番号
US09394264B2

反応ノート

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