Bromine → 1-Bromo-4-cyclopropylbenzene

HRID 1830929

反応式

HRID 1830929 の反応式
[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

参加物

7

反応物 4

HCID 24408BromineHCID 70112CyclopropylbenzeneHCID 517045Sodium AcetateHCID 23665763Sodium Bisulfite

生成物 1

HCID 122213551-Bromo-4-cyclopropylbenzene収率 21%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒2 回HCID 962Water溶媒

実験手順

Cyclopropyl benzene (48.5 g, 410 mmol), glacial acetic acid (510 mL), and sodium acetate (38.9 g, 474 mmol) were added to a roundbottomed 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).

後処理

  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

出典と根拠

ORDレコード
ord-80817b994af840d69ffb93a89a418796
出典データセット
uspto-grants-2006_06
特許番号
US07067539B2

関連ノート

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