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

HRID 658095ノート

反応式

HRID 658095 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-d3424850e7084df9b99bb89841dd8669
出典データセット
uspto-grants-2011_12
特許番号
US08076367B2

反応ノート

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