Acetonitrile → HCID 66608287, 화합물

HRID 218983노트

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HRID 218983 반응식
C(#N)C.[Br:4][C:5]1[CH:6]=[CH:7][C:8]([F:22])=[C:9]([CH:11](Cl)[C:12]2[S:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[CH:16]=2)[CH:10]=1.[BH4-].[Na+].[OH-].[Na+]>O>[Br:4][C:5]1[CH:6]=[CH:7][C:8]([F:22])=[C:9]([CH:10]=1)[CH2:11][C:12]1[S:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[CH:16]=1

참가 물질

6

반응물 4

HCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 249881712-((5-Bromo-2-fluorophenyl)chloromethyl)benzo(b)thiophene

생성물 1

HCID 66608287HCID 66608287, 화합물수율 80.9%

시약·촉매·용매 1

HCID 962Water용매

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온도
40 °C

실험 절차

Acetonitrile (1,260 ml) was added to 2-[(5-bromo-2-fluorophenyl)(chloro)methyl]-1-benzothiophene (265.69 g) and the mixture was heated to 40° C. The resulting solution was added to a water (1,260 ml) solution of sodium borohydride (113.0 g) and sodium hydroxide (14.9 g) at 59.0 to 67.9° C., followed by stirring at 24.1 to 67.5° C. for 17.5 hours. To the reaction mixture were added 36% hydrochloric acid (340.5 g), water (1,260 ml) and toluene (1,260 ml), and extraction was conducted. The organic layer was washed with a 5% aqueous sodium hydrogencarbonate solution (1,260 ml) and subjected to vacuum distillation to distil off the solvent. To the residue were added 2-propanol (378 ml) and methanol (756 ml), and the residue was dissolved with heating. To the solution was added, as a seed crystal, 2.7 g of the 2-(5-bromo-2-fluorobenzyl)-1-benzothiophene produced by the method of Reference Example 2, at 39.7° C., followed by stirring at 0.7 to 5.0° C. for 13 hours. The separated-out crystals were collected by filtration, washed with methanol (251 ml), and vacuum-dried to obtain, as white crystals, 2-(5-bromo-2-fluorobenzyl)-1-benzothiophene [194.05 g, yield: 80.9%, purity: 99% (HPLC)].

후처리

  1. additionTo the reaction mixture were added
  2. extraction36% hydrochloric acid (340.5 g), water (1,260 ml) and toluene (1,260 ml), and extraction
  3. washThe organic layer was washed with a 5% aqueous sodium hydrogencarbonate solution (1,260 ml)
  4. distillationsubjected to vacuum distillation
  5. customto distil off the solvent
  6. additionTo the residue were added 2-propanol (378 ml) and methanol (756 ml)
  7. dissolutionthe residue was dissolved
  8. temperaturewith heating
  9. additionTo the solution was added, as a seed crystal, 2.7 g of the 2-(5-bromo-2-fluorobenzyl)-1-benzothiophene
  10. customproduced by the method of Reference Example 2, at 39.7° C.
  11. stirringby stirring at 0.7 to 5.0° C. for 13 hours
  12. filtrationThe separated-out crystals were collected by filtration
  13. washwashed with methanol (251 ml)
  14. customvacuum-dried

출처 및 근거

ORD 기록
ord-d9c05915fb514a8ab2eb719d32a1998b
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198464B2

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