Allyl bromide → Methyl 2-(2-chloro-4-fluorophenyl)pent-4-enoate

HRID 451518노트

반응식

HRID 451518 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([O:12][CH3:13])=[O:11].[CH2:14](Br)[CH:15]=[CH2:16]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH2:16][CH:15]=[CH2:14])[C:10]([O:12][CH3:13])=[O:11]

참가 물질

4

반응물 2

HCID 7841Allyl bromideHCID 736123(2-Chloro-4-fluorophenyl)acetic acid methyl ester

생성물 1

HCID 67342147Methyl 2-(2-chloro-4-fluorophenyl)pent-4-enoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a chilled (−78° C.) solution of lithium hexamethydisilylazide (27.1 mL, 1 M in THF, 27.1 mmol) in THF (30 mL) was added methyl 2-(2-chloro-4-fluorophenyl)acetate (5 g, 24.7 mmol) in THF (10 mL). After stirring for 0.5 hour, allyl bromide (2.4 mL, 27.1 mmol) was added in a single portion, the cooling bath removed and the reaction allowed to warm to room temperature (0.5 hour). The reaction was diluted with ethyl acetate, washed with water, brine, and the organic phase was dried with sodium sulfate and the solvent was evaporated in vacuo. The residue was purified by column chromatography on silica gel using n-heptane/ethyl acetate (v/v 1:0 to 9:1) as eluent. The title compound was obtained as a colourless liquid (6.0 g, 100%).

후처리

  1. customthe cooling bath removed
  2. additionThe reaction was diluted with ethyl acetate
  3. washwashed with water, brine
  4. dry with materialthe organic phase was dried with sodium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-4e326ceebe6c49219fba7618bae5416d
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486967B2

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