Sulfuric Acid → N-[3-(2-Bromoacetyl)-5-(pentafluorosulfanyl)phenyl]acetamide

HRID 532357ノート

反応式

HRID 532357 の反応式
[C:1]([C:4]1[CH:5]=[C:6]([NH:16][C:17](=[O:19])[CH3:18])[CH:7]=[C:8]([S:10]([F:15])([F:14])([F:13])([F:12])[F:11])[CH:9]=1)(=[O:3])[CH3:2].[Br-:20].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.S(=O)(=O)(O)O>CO.C1COCC1>[Br:20][CH2:2][C:1]([C:4]1[CH:5]=[C:6]([NH:16][C:17](=[O:19])[CH3:18])[CH:7]=[C:8]([S:10]([F:11])([F:12])([F:13])([F:14])[F:15])[CH:9]=1)=[O:3]

参加物

6

反応物 3

HCID 1118Sulfuric AcidHCID 17977687Phenyltrimethylammonium bromide dibromideHCID 58136897N-[3-Acetyl-5-(pentafluorosulfanyl)phenyl]acetamide

生成物 1

HCID 58136929N-[3-(2-Bromoacetyl)-5-(pentafluorosulfanyl)phenyl]acetamide収率 76.5%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

N-[3-Acetyl-5-(pentafluorosulfanyl)phenyl]acetamide (859 mg, for synthesis see example 1) was dissolved in a mixture of methanol (10 ml) and THF (10 ml) and phenyltrimethylammonium tribromide (1.065 g) was added in portions while stirring. After stirring at RT for 2 h, the mixture was heated to 40° C. for a further 3 h. After cooling, the reaction mixture was added to 2 N sulfuric acid and the aqueous phase was extracted 3 times with ethyl acetate. The combined extracts were dried over sodium sulfate, filtered and concentrated. The crude product was purified using silica gel with ethyl acetate/heptane as the eluent. 480 mg of the desired compound were obtained. LC-MS rt: 1.47 min [M+H]+: 382.0 (met. a)

後処理

  1. additionwas added in portions
  2. stirringAfter stirring at RT for 2 h
  3. temperatureAfter cooling
  4. extractionthe aqueous phase was extracted 3 times with ethyl acetate
  5. dry with materialThe combined extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified

出典と根拠

ORDレコード
ord-f48f578fa6e34f9085054dfc5d2b7ce4
出典データセット
uspto-grants-2014_10
特許番号
US08853206B2

反応ノート

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