5-Bromo-2-fluorobenzaldehyde → 4-Bromo-2-ethenyl-1-fluorobenzene

HRID 1241762ノート

反応式

HRID 1241762 の反応式
[CH3:1]C(C)([O-])C.[K+].[Br:7][C:8]1[CH:9]=[CH:10][C:11]([F:16])=[C:12]([CH:15]=1)[CH:13]=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([F:16])=[C:12]([CH:15]=1)[CH:13]=[CH2:1]

参加物

5

反応物 2

HCID 7363275-Bromo-2-fluorobenzaldehydeHCID 23665647Potassium tert-butoxide

生成物 1

HCID 219339834-Bromo-2-ethenyl-1-fluorobenzene収率 90%

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of methyltriphenylphosphonium bromide (2.14 g, 6 mmol) and potassium t-butoxide (672 mg, 6 mmol) in 50 mL of THF was refluxed for 30 minutes under N2 and then cooled to room temperature. 5-Bromo-2-fluorobenzaldehyde (1.02 g, 5 mmol) was added and the resulting mixture was refluxed for 2 hours (until the TLC showed the disappearance of starting aldehyde). The reaction was concentrated in vacuo and partitioned between water and ethyl acetate. The acetate layer was washed with water and brine. The solution was dried over MgSO4 and concentrated in vacuo. The residue was purified by chromatography (silica gel, 15:1 hexanes-diethyl ether) to provide 900 mg (90%) of 5-bromo-2-fluorostyrene.

後処理

  1. temperaturewas refluxed for 30 minutes under N2
  2. temperaturethe resulting mixture was refluxed for 2 hours (until the TLC
  3. concentrationThe reaction was concentrated in vacuo
  4. custompartitioned between water and ethyl acetate
  5. washThe acetate layer was washed with water and brine
  6. dry with materialThe solution was dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography (silica gel, 15:1 hexanes-diethyl ether)

出典と根拠

ORDレコード
ord-deec79f1804a4ca4a0de6e77ef4d3f82
出典データセット
uspto-grants-2006_10
特許番号
US07115591B2

反応ノート

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