Water → 3-Bromo-4-(trifluoromethoxy)benzoic acid

HRID 2040531ノート

反応式

HRID 2040531 の反応式
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1.[Br:15]Br.O>[N+](C)([O-])=O.[Fe](Cl)(Cl)Cl>[Br:15][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:4]=1[O:3][C:2]([F:13])([F:14])[F:1])[C:8]([OH:10])=[O:9]

参加物

6

反応物 3

HCID 962WaterHCID 24408BromineHCID 676134-(Trifluoromethoxy)benzoic acid

生成物 1

HCID 202740913-Bromo-4-(trifluoromethoxy)benzoic acid収率 54.3%

試薬・触媒・溶媒 2

HCID 24380Iron chloride (FeCl3)触媒HCID 6375Nitromethane溶媒

反応条件

温度
110 °C

実験手順

4-(Trifluoromethoxy)benzoic acid (2 g, 9.70 mmol) and iron(III) chloride (1.574 g, 9.70 mmol) were suspended in nitromethane (20 mL). To this mixture was added bromine (0.497 mL, 9.70 mmol) at 0° C. The solution was heated under microwave irradiation at 110° C. for 2 h. The reaction mixture was added to cold water (100 mL) and extracted with ethylacetate (2×100 mL). The organic phase was washed with an aqueous solution of sodium thiosulfate pentahydrate and brine. The organic layer was concentrated and the residue was purified by HPLC to give the title compound as a white solid (1.5 g). LCMS m/z=287.0 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.67 (d, 1H), 8.06 (d, 1H), 8.29 (s, 1H), 13.47 (s, 1H).

後処理

  1. extractionextracted with ethylacetate (2×100 mL)
  2. washThe organic phase was washed with an aqueous solution of sodium thiosulfate pentahydrate and brine
  3. concentrationThe organic layer was concentrated
  4. customthe residue was purified by HPLC

出典と根拠

ORDレコード
ord-912725ab229247448828ea2a3f926a2c
出典データセット
uspto-grants-2013_11
特許番号
US08580841B2

反応ノート

読み込み中…