3-Chlorobenzaldehyde → (4-Bromo-2,5-dichloro-3-thienyl)(3-chlorophenyl)methanol

HRID 870047노트

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HRID 870047 반응식
Br[C:2]1[C:6]([Br:7])=[C:5]([Cl:8])[S:4][C:3]=1[Cl:9].[Li]CCCC.[Cl:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH:19]=[O:20]>C1COCC1>[Br:7][C:6]1[C:2]([CH:19]([C:18]2[CH:21]=[CH:22][CH:23]=[C:16]([Cl:15])[CH:17]=2)[OH:20])=[C:3]([Cl:9])[S:4][C:5]=1[Cl:8]

참가 물질

5

반응물 3

HCID 114773-ChlorobenzaldehydeHCID 70153183,4-Dibromo-2,5-dichlorothiopheneHCID 178418339Butyllithium

생성물 1

HCID 57900988(4-Bromo-2,5-dichloro-3-thienyl)(3-chlorophenyl)methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

To a solution of 3,4-dibromo-2,5-dichlorothiophene (2.00 g, 6.43 mmol) in THF (18 mL) at −78° C., was added n-BuLi (2.5M in hexane, 2.57 mL, 6.43 mmol) dropwise. After 30 min., 3-chlorobenzaldehyde (0.732 mL, 6.43 mmol) was added dropwise to the yellow solution. The resulting solution was stirred at −78° C. for 30 min. and allowed to warm to 0° C. After 30 min., the reaction was quenched by the addition of 25% aq. NH4OAc. The aqueous layer was extracted with EtOAc and the combined organics were washed with water and brine, dried (Na2SO4) and concentrated. The crude product was purified by chromatography on silica gel (50:50 to 80:20 CHCl3/hexane) to afford the desired product as a pale yellow oil.

후처리

  1. temperatureto warm to 0° C
  2. waitAfter 30 min.
  3. customthe reaction was quenched by the addition of 25% aq. NH4OAc
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washthe combined organics were washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe crude product was purified by chromatography on silica gel (50:50 to 80:20 CHCl3/hexane)

출처 및 근거

ORD 기록
ord-5ec3e8f4ff7345f4b17b6326447c023e
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969394B2

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