Ethanol → 3-Bromo-5-(trifluoromethoxy)benzoic acid

HRID 2216769ノート

反応式

HRID 2216769 の反応式
N[C:2]1[C:10]([O:11][C:12]([F:15])([F:14])[F:13])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[Br:16].C(O)C.S(=O)(=O)(O)O.N([O-])=O.[Na+]>O>[Br:16][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:11][C:12]([F:13])([F:14])[F:15])[CH:2]=1)[C:6]([OH:8])=[O:7]

参加物

6

反応物 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 219424074-Amino-3-bromo-5-(trifluoromethoxy)benzoic acidHCID 23668193Sodium Nitrite

生成物 1

HCID 27828433-Bromo-5-(trifluoromethoxy)benzoic acid収率 75.8%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

4-Amino-3-bromo-5-trifluoromethoxybenzoic acid (1.5 g, 5 mmoles) was mixed with ethanol (15 mL) at 0° C. and then concentrated sulfuric acid (2.26 g, 10.2 mmoles) wad added. The sodium nitrite (0.38 g, 5.5 mmoles) water solution (1.2 mL) was added dropwise at 0° C. for 1 hour. After the reaction mixture was warmed to room temperature and then heated to reflux for 45 minutes, water was added. The mixture was extracted with dichloromethane. The dichloromethane layer was dried and concentrated. The residue was dissolved in 1M sodium hydroxide and extracted with ether. The aqueous solution was acidified with 2M HCl to pH=2 to give 3-bromo-5-trifluoromethoxybenzoic acid (1.08 g, 75.5%).

後処理

  1. temperatureheated
  2. temperatureto reflux for 45 minutes
  3. extractionThe mixture was extracted with dichloromethane
  4. dry with materialThe dichloromethane layer was dried
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in 1M sodium hydroxide
  7. extractionextracted with ether

出典と根拠

ORDレコード
ord-829b86b4d17541e18a755fc5ffd0b3d4
出典データセット
uspto-grants-2006_09
特許番号
US07112595B2

反応ノート

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