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

HRID 451518ノート

反応式

HRID 451518 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-4e326ceebe6c49219fba7618bae5416d
出典データセット
uspto-grants-2013_07
特許番号
US08486967B2

反応ノート

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