Formic Acid → 7-Bromo-2,3-dihydrobenzofuran-3-ol

HRID 469165ノート

反応式

HRID 469165 の反応式
C(N(CC)CC)C.C(O)=O.[Br:11][C:12]1[C:20]2[O:19][CH2:18][C:17](=[O:21])[C:16]=2[CH:15]=[CH:14][CH:13]=1.C(OCC)(=O)C>C(Cl)Cl.O>[Br:11][C:12]1[C:20]2[O:19][CH2:18][CH:17]([OH:21])[C:16]=2[CH:15]=[CH:14][CH:13]=1

参加物

7

反応物 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 41378967-BROMO-3-BENZOFURANONE

生成物 1

HCID 657210567-Bromo-2,3-dihydrobenzofuran-3-ol収率 94.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

Triethylamine (0.2 ml) was added to formic acid (63 μl), to the resultant mixture, a solution in methylene chloride (2.1 ml) of 7-bromo-2,3-dihydrobenzofuran-3-one (0.10 g) that is commercially available or can be obtained by a publicly known method was added, chloro[(1S,2S)—N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine]-(mesitylene) ruthenium (II) (8.8 mg) was added, and the resultant mixture was stirred at room temperature for 3 hours. To the resultant mixture, ethyl acetate and water were added, followed by extracting the resultant mixture with ethyl acetate, and the organic phase was washed with a saturated saline, and then was dried over anhydrous sodium sulfate. From the organic phase, the solvent was distilled off under reduced pressure, followed by purifying the resultant residue by silica gel column chromatography (eluate; n-hexane:ethyl acetate=5:1 to 3:1), and from the resultant, the solvent was distilled off under reduced pressure to obtain the subject compound (95 mg) as pale orange oil.

後処理

  1. customcan be obtained by a publicly known method
  2. additionwas added
  3. extractionby extracting the resultant mixture with ethyl acetate
  4. washthe organic phase was washed with a saturated saline
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. distillationFrom the organic phase, the solvent was distilled off under reduced pressure
  7. customby purifying the resultant residue by silica gel column chromatography (eluate; n-hexane:ethyl acetate=5:1 to 3:1)
  8. distillationfrom the resultant, the solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-74cd163c19ee471c9f6c56e4f6b5c76f
出典データセット
uspto-grants-2014_01
特許番号
US08629102B2

反応ノート

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