Ammonium Chloride → Tert-butyl 2,4-difluoro-3-vinylbenzoate

HRID 2233769ノート

反応式

HRID 2233769 の反応式
[CH2:1]([Li])CCC.C1COCC1.[I-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[F:32][C:33]1[C:45]([CH:46]=O)=[C:44]([F:48])[CH:43]=[CH:42][C:34]=1[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36].[Cl-].[NH4+]>C1COCC1>[F:32][C:33]1[C:45]([CH:46]=[CH2:1])=[C:44]([F:48])[CH:43]=[CH:42][C:34]=1[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36]

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 638159Methyltriphenylphosphonium iodideHCID 86626216Tert-butyl 2,4-difluoro-3-formylbenzoateHCID 178420697HCID 178420697、化合物

生成物 1

HCID 68451303Tert-butyl 2,4-difluoro-3-vinylbenzoate収率 50%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

At −78° C., 9.50 ml of 1.59 M n-butyl lithium-THF solution was added dropwise to 90 ml of THF solution containing 8.13 g of methyltriphenylphosphonium iodide. This was stirred at 0° C. for 10 minutes, cooled to −78° C. and then mixed with 2.44 g of tert-butyl 2,4-difluoro-3-formylbenzoate dissolved in 10 ml of THF. After 40 minutes thereof, this was stirred at room temperature for 1 hour, mixed with appropriate amounts of saturated ammonium chloride aqueous solution and purified water, extracted with ethyl acetate and then dried with anhydrous magnesium sulfate. After concentration, the thus formed residue was purified by a silica gel column chromatography to obtain 1.20 g (50%) of tert-butyl 2,4-difluoro-3-vinylbenzoate (Reference Example 5-1) from a hexane-ethyl acetate (50:1) eluate. ES−: 239

後処理

  1. temperaturecooled to −78° C.
  2. waitAfter 40 minutes
  3. stirringthis was stirred at room temperature for 1 hour
  4. custompurified water
  5. extractionextracted with ethyl acetate
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationAfter concentration
  8. customthe thus formed residue was purified by a silica gel column chromatography

出典と根拠

ORDレコード
ord-6844445b3fb140778e4764510d4da8c6
出典データセット
uspto-grants-2010_05
特許番号
US07709519B2

反応ノート

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