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

HRID 915895노트

반응식

HRID 915895 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

실험 절차

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]−).

후처리

  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

출처 및 근거

ORD 기록
ord-473ab8e3c86245039f8a02bd209ae7fe
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07268149B2

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