Hydrochloric Acid → Methyl trans-2-(4-bromobenzoyl)cyclopropanecarboxylate

HRID 9544

반응식

HRID 9544 반응식
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C@@H:8]2[CH2:10][C@H:9]2[C:11]([OH:13])=[O:12])=[O:7])=[CH:4][CH:3]=1.[CH3:16]OC(OC)(C)C.Cl>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C@@H:8]2[CH2:10][C@H:9]2[C:11]([O:13][CH3:16])=[O:12])=[O:7])=[CH:14][CH:15]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 64952,2-DimethoxypropaneHCID 58681322trans-2-(4-Bromobenzoyl)cyclopropanecarboxylic acid

생성물 1

HCID 58681311Methyl trans-2-(4-bromobenzoyl)cyclopropanecarboxylate수율 83.5%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
40 °C

실험 절차

To a solution of trans-2-(4-bromobenzoyl)cyclopropanecarboxylic acid (9.43 g, 32.59 mmol) in MeOH (200 mL) was added 2,2-dimethoxypropane (10.18 g, 97.77 mmol) and HCl (4.0 M in dioxane, 4.0 mL). The resulting solution was stirred at 40° C. overnight, and then evaporated to dryness. The resulting residue was purified by flash chromatography (Biotage Flash 40M) using 15 to 25% ethyl acetate in hexanes to afford methyl trans-2-(4-bromobenzoyl)cyclopropanecarboxylate (7.7 g, 83%). 1H NMR (400 MHz, CD2Cl2) δ 1.68 (m, 2H), 2.37 (m, 1H), 3.21 (m, 1H), 3.65 (s, 3H), 7.68 (m, 2H), 7.90 (m, 2H).

후처리

  1. customevaporated to dryness
  2. customThe resulting residue was purified by flash chromatography (Biotage Flash 40M)

출처 및 근거

ORD 기록
ord-8a764fe4df3f4c62aea42b76e9d94364
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091228B2

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