2-Aminophenol → 3-bromo-N-(2-hydroxyphenyl)4-methylbenzamide

HRID 7681

反応式

HRID 7681 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=O.S(Cl)(Cl)=O.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23].C(N(C(C)C)CC)(C)C>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23])=[O:7]

参加物

6

反応物 4

HCID 58012-AminophenolHCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 821303-Bromo-4-methylbenzoic acid

生成物 1

HCID 219909653-bromo-N-(2-hydroxyphenyl)4-methylbenzamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 3-bromo-4-methylbenzoic acid (1.0 g, 4.7 mmol) and thionyl chloride (18 mL) was refluxed for 1 h and then cooled to rt. The excess thionyl chloride was removed in vacuo, the residue was dissolved in THF (10 mL), and was added to a cooled (0° C.) mixture of 2-aminophenol (510 mg, 4.7 mmol) and diisopropylethylamine (0.90 mL, 5.1 mmol) in THF (18 mL). The resulting mixture was stirred at rt for 4 h. The solvent was then removed and the residue was purified by flash chromatography on silica gel eluting with EtOAc:hexane (1:5 to 1:4) to afford 3-bromo-N-(2-hydroxyphenyl)-4-methylbenzamide.

後処理

  1. temperaturewas refluxed for 1 h
  2. customThe excess thionyl chloride was removed in vacuo
  3. dissolutionthe residue was dissolved in THF (10 mL)
  4. additionwas added to
  5. temperaturea cooled
  6. customThe solvent was then removed
  7. customthe residue was purified by flash chromatography on silica gel eluting with EtOAc:hexane (1:5 to 1:4)

出典と根拠

ORDレコード
ord-e4a2a72cc2724411b370e0075895332a
出典データセット
uspto-grants-2006_08
特許番号
US07087601B2

関連ノート

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