Sodium Acetate → 2,6-Dibromobenzyl acetate

HRID 409372

반응식

HRID 409372 반응식
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[CH2:9]Br.[CH3:11][C:12]([O-:14])=[O:13].[Na+]>CN(C)C=O>[C:12]([O:14][CH2:9][C:3]1[C:4]([Br:8])=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])(=[O:13])[CH3:11]

참가 물질

4

반응물 2

HCID 517045Sodium AcetateHCID 133810151,3-Dibromo-2-(bromomethyl)benzene

생성물 1

HCID 592164132,6-Dibromobenzyl acetate수율 95%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

A mixture of 1,3-dibromo-2-(bromomethyl)benzene (27.6 g, 84 mmol), NaOAc (35.5 g, 5 eq.) and dimethylformamide (DMF) (150 mL) was stirred at 100° C. (hot oil bath temperature) for 1.75 h, allowed to cool, and then partitioned between heptane (500 mL) and water (200 mL). After removing the organic layer, the aqueous layer was extracted with heptane (200 mL). The combined organics were washed with H2O (2×300 mL), dried (Na2SO4), filtered, and evaporated to give 24.57 g (yield of 95%) of title product as a colorless oil. This oil contained 13% unreacted starting material but was successfully used without further purification. 1H NMR (300 MHz, CDCl3) δ 2.10 (s, 3H), 5.41 (s, 2H), 7.08 (t, 1H), 7.58 (d, 2H).

후처리

  1. temperatureto cool
  2. custompartitioned between heptane (500 mL) and water (200 mL)
  3. customAfter removing the organic layer
  4. extractionthe aqueous layer was extracted with heptane (200 mL)
  5. washThe combined organics were washed with H2O (2×300 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated

출처 및 근거

ORD 기록
ord-be467ddb4b66466d8687c9f381268551
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759340B2

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