Boron tribromide → 6-Hydroxy-7-fluoro-2,2-dimethylthiochroman-4-one

HRID 619611ノート

反応式

HRID 619611 の反応式
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[F:13])[S:9][C:8]([CH3:15])([CH3:14])[CH2:7][C:6]2=[O:16].B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[F:13])[S:9][C:8]([CH3:14])([CH3:15])[CH2:7][C:6]2=[O:16]

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 218466566-Methoxy-7-fluoro-2,2-dimethyl-thiochroman-4-one2 回

生成物 1

HCID 218466896-Hydroxy-7-fluoro-2,2-dimethylthiochroman-4-one収率 68%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-230 °C

実験手順

To a solution of 6-methoxy-7-fluoro-2,2-dimethyl-thiochroman-4-one (Compound 203, 1.75 g, 7.29 mmol) in 25 mL CH2Cl2 cooled to -23° C. was added BBr3 (5.46 g, 21.8 mmol; 21.8 mL of a 1M solution in CH2Cl2) over a 10 minute period. After stirring for 23 hours at -230° C. the solution was warmed to 0° C. for 3 hours, and then cooled to -78° C. and quenched by the slow addition of 25 mL of H2O. Upon warming to room temperature the aqueous layer was extracted with CH2Cl2 and the combined organic layers were washed with saturated aqueous NaHCO3, H2O, and saturated aqueous NaCl before being dried over MgSO4. Removal of the solvents under reduced pressure, followed by column chromatography (10 to 20% EtOAc/hexanes) afforded 1.12 g (68%) of the title compound as a colorless solid. 1H NMR (300 MHz, CDCl3)δ: 7.82 (1H, d J=9.3 Hz), 6.97 (1H, d, J=10.4 Hz), 5.54 (1H, s), 2.86 (2H,s), 1.46 (6H, s).

後処理

  1. temperaturewas warmed to 0° C. for 3 hours
  2. temperaturecooled to -78° C.
  3. customquenched by the slow addition of 25 mL of H2O
  4. temperatureUpon warming to room temperature the aqueous layer
  5. extractionwas extracted with CH2Cl2
  6. washthe combined organic layers were washed with saturated aqueous NaHCO3, H2O, and saturated aqueous NaCl
  7. dry with materialbefore being dried over MgSO4
  8. customRemoval of the solvents under reduced pressure

出典と根拠

ORDレコード
ord-5ada0b9a1c714770b6a6937cebfd340c
出典データセット
uspto-grants-1999_09
特許番号
US05958954

反応ノート

読み込み中…