Hydrochloric Acid → HCID 66608287、化合物

HRID 218980ノート

反応式

HRID 218980 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:19])=[C:6]([CH:8](Cl)[C:9]2[S:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[CH:13]=2)[CH:7]=1.[BH4-].[Na+].[OH-].[Na+].Cl>O.C1(C)C=CC=CC=1.O1CCOCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:19])=[C:6]([CH:7]=1)[CH2:8][C:9]1[S:10][C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[CH:13]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 249881712-((5-Bromo-2-fluorophenyl)chloromethyl)benzo(b)thiophene

生成物 1

HCID 66608287HCID 66608287、化合物収率 75%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 1140Toluene溶媒HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
56 °C

実験手順

A dioxane (1.1 liters) solution of 2-[(5-bromo-2-fluorophenyl)(chloro)methyl]-1-benzothiophene (551 g) was added to a dioxane (3.3 liters)-water (1.6 liters) solution of sodium borohydride (410 g) and sodium hydroxide (31 g) at 60 to 66° C., followed by stirring at 52 to 60° C. for 39 hours. To the reaction mixture was added toluene (5.5 liter), water (3.8 liters) and 36% hydrochloric acid (620 ml) to conduct extraction. The organic layer was subjected to distillation under reduced pressure to distil off the solvent. The residue was dried under reduced pressure. The obtained crystals were dissolved in 2-propanol (1 liter) and methanol (1 liter) with heating, followed by stirring at 0° C. for 20.5 hours. The separated-out crystals were collected by filtration, washed with methanol (500 ml), and dried under reduced pressure to obtain 2-(5-bromo-2-fluorobenzyl)-1-benzothiophene [373 g, yield: 75.0%, purity: 99% (HPLC)] as white crystals. Incidentally, the 2-[(5-bromo-2-fluorophenyl)(chloro)methyl]-1-benzothiophene is the same as the compound (5) obtained in the second step of the production method of the present invention.

後処理

  1. extractionextraction
  2. distillationThe organic layer was subjected to distillation under reduced pressure
  3. customto distil off the solvent
  4. customThe residue was dried under reduced pressure
  5. dissolutionThe obtained crystals were dissolved in 2-propanol (1 liter)
  6. temperaturemethanol (1 liter) with heating
  7. stirringby stirring at 0° C. for 20.5 hours
  8. filtrationThe separated-out crystals were collected by filtration
  9. washwashed with methanol (500 ml)
  10. customdried under reduced pressure

出典と根拠

ORDレコード
ord-7750ffc502b844f8a9ef56c2ff104d50
出典データセット
uspto-grants-2012_06
特許番号
US08198464B2

反応ノート

読み込み中…