Bromine → 6-bromospiro[3,1-benzoxazine-4,1'-cyclobutan]-2(1H)-one

HRID 915895ノート

反応式

HRID 915895 の反応式
[C:1]12([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[NH:7][C:6](=[O:14])[O:5]1)[CH2:4][CH2:3][CH2:2]2.C([O-])(=O)C.[K+].[Br:20]Br>C(O)(=O)C>[Br:20][C:11]1[CH:12]=[CH:13][C:8]2[NH:7][C:6](=[O:14])[O:5][C:1]3([CH2:4][CH2:3][CH2:2]3)[C:9]=2[CH:10]=1

参加物

5

反応物 3

HCID 24408BromineHCID 517044Potassium AcetateHCID 18442664Spiro[3,1-benzoxazine-4,1'-cyclobutan]-2(1H)-one

生成物 1

HCID 112426146-bromospiro[3,1-benzoxazine-4,1'-cyclobutan]-2(1H)-one収率 53%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

実験手順

To a solution of spiro[3,1-benzoxazine-4,1′-cyclobutan]-2(1H)-one (0.36 g, 1.9 mmol) and potassium acetate (0.56 g, 5.7 mmol) in acetic acid was added a solution of bromine (0.09 mL, 1.95 mmol) in acetic acid (2 mL) at room temperature. Upon completion by TLC of the reaction, the acetic acid was removed. The residue was treated with saturated sodium bicarbonate (100 mL) and the product extracted with ethyl acetate (50 mL). The organics were dried over magnesium sulfate and concentrated. Trituration of residue with ether gave 6-bromospiro[3,1-benzoxazine-4,1′-cyclobutan]-2(1H)-one (0.27 g, 52%) as a white solid. 1H NMR (DMSO-d6): δ 10.37 (s, 1H), 7.65 (d, 1H, J=2.1 Hz), 7.47 (dd, 1H, J=8.5, 2.2 Hz) 6.86 (d, 1H, J=8.5 Hz), 2.52-2.47 (m, 2H), 2.04-1.98 (m, 2H), 1.87-1.80 (m, 2H). MS (ESI) m/z 268/270 ([M+H]+); MS (ESI) m/z 266/268 ([M−H]−).

後処理

  1. customUpon completion by TLC of the reaction
  2. customthe acetic acid was removed
  3. additionThe residue was treated with saturated sodium bicarbonate (100 mL)
  4. extractionthe product extracted with ethyl acetate (50 mL)
  5. dry with materialThe organics were dried over magnesium sulfate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-473ab8e3c86245039f8a02bd209ae7fe
出典データセット
uspto-grants-2007_09
特許番号
US07268149B2

反応ノート

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