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m-Chloroperbenzoic acid → 2-Bromo-5-methylpyridine 1-oxide

HRID 541422
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HRID 541422 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.C1C=C(Cl)C=C(C(OO)=[O:17])C=1>ClCCl.[OH-].[Na+]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N+:3]=1[O-:17]
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참가 물질

5

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 5642162-Bromo-5-methylpyridine

생성물 1

HCID 131787372-Bromo-5-methylpyridine 1-oxide

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 14798Sodium Hydroxide용매2회

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온도
30 °C

실험 절차

Into a round-bottom flask, was placed a solution of 2-bromo-5-methylpyridine (10.0 g, 58.1 mmol, 1.00 equiv) in dichloromethane (250 mL). mCPBA (15.0 g, 86.9 mmol, 1.50 equiv) was added in several batches at room temperature. The resulting solution was stirred overnight at 30° C., then diluted with 50 mL of 2N sodium hydroxide (aq.). The pH value of the solution was adjusted to 10 with 2N sodium hydroxide (aq.). The aqueous phase was extracted with 3×100 mL of dichloromethane and the combined organic layers were dried over anhydrous magnesium sulfate and concentrated under reduced pressure to yield 11.0 g (91%) of 2-bromo-5-methylpyridin-1-ium-1-olate as a yellow solid.

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후처리

  1. customInto a round-bottom flask, was placed
  2. extractionThe aqueous phase was extracted with 3×100 mL of dichloromethane
  3. dry with materialthe combined organic layers were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto yield 11.0 g (91%) of 2-bromo-5-methylpyridin-1-ium-1-olate as a yellow solid

출처 및 근거

ORD 기록
ord-dd0389c101d74488b83f58d19e2af4bc
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08871790B2

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