Bromine → 1-Bromo-4-cyclopropylbenzene

HRID 1786661

반응식

HRID 1786661 반응식
[CH:1]1([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.C([O-])(=O)C.[Na+].[Br:15]Br.OS([O-])=O.[Na+]>C(O)(=O)C.O>[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([Br:15])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

참가 물질

7

반응물 4

HCID 24408BromineHCID 70112CyclopropylbenzeneHCID 517045Sodium AcetateHCID 23665763Sodium Bisulfite

생성물 1

HCID 122213551-Bromo-4-cyclopropylbenzene수율 21%

시약·촉매·용매 2

HCID 176Acetic Acid용매2회HCID 962Water용매

실험 절차

Cyclopropyl benzene (48.5 g, 410 mmol), glacial acetic acid (510 mL), and sodium acetate (38.9 g, 474 mmol) were added to a round bottomed flask. The flask was cooled in an ice-water bath. A solution of bromine (66.3 g, 414 mmol) dissolved in 105 mL of acetic acid was added dropwise over 90 min. The reaction mixture was stirred at temperatures between 0° C. and 10° C. for 5 h. The reaction was then allowed to warm to rt overnight. Hexanes (1300 mL) and water (250 mL) were added. Aqueous NaHSO3 (1M) was added until the reaction mixture changed from yellow to clear. The layers were separated. The organic layer was washed with water, 1M aq Na2CO3, and brine, then dried with Na2SO4. The solvent was evaporated and the crude product was purified via sgc using hexanes as the mobile phase to give 17 g of p-cyclopropylbromobenzene (21%) (Compound 44).

후처리

  1. temperatureThe flask was cooled in an ice-water bath
  2. additionwas added dropwise over 90 min
  3. customThe layers were separated
  4. washThe organic layer was washed with water, 1M aq Na2CO3, and brine
  5. dry with materialdried with Na2SO4
  6. customThe solvent was evaporated
  7. customthe crude product was purified via sgc

출처 및 근거

ORD 기록
ord-d454e0aadbda429e85a9206ac6fc1e6f
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07507767B2

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