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

HRID 458555ノート

反応式

HRID 458555 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-9be73ecf89dc42daa02f1e1a56f270de
出典データセット
uspto-grants-2007_03
特許番号
US07192956B2

反応ノート

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