Hydrogen Bromide → 2,4'-Difluoro-3-hydroxy-[1,1'-biphenyl]-4-carbaldehyde

HRID 531134노트

반응식

HRID 531134 반응식
Br.[F:2][C:3]1[C:8]([O:9]C)=[C:7]([CH:11]=[O:12])[CH:6]=[CH:5][C:4]=1[C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1>C(O)(=O)C>[F:2][C:3]1[C:8]([OH:9])=[C:7]([CH:11]=[O:12])[CH:6]=[CH:5][C:4]=1[C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1

참가 물질

4

반응물 2

HCID 260Hydrogen BromideHCID 904236032,4'-Difluoro-3-methoxybiphenyl-4-carbaldehyde

생성물 1

HCID 904239512,4'-Difluoro-3-hydroxy-[1,1'-biphenyl]-4-carbaldehyde수율 94.5%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
120 °C

실험 절차

48% hydrobromic acid (28.4 mL) was added at room temperature to an acetic acid (150 mL) solution of 2,4′-difluoro-3-methoxybiphenyl-4-carbaldehyde (6.18 g), and the mixture was stirred at 120° C. for 18 hours in a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and then, the solvent was distilled off under reduced pressure. The obtained residue was diluted with ethyl acetate and water. The organic layer was separated, and then, the obtained aqueous layer was neutralized with a 1 M aqueous sodium hydroxide solution, followed by extraction with ethyl acetate. Combined organic layers were washed with water and saturated saline in this order and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was passed through a short silica gel column (hexane/ethyl acetate) to obtain the title compound (5.51 g).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionThe obtained residue was diluted with ethyl acetate and water
  4. customThe organic layer was separated
  5. extractionfollowed by extraction with ethyl acetate
  6. washCombined organic layers were washed with water and saturated saline in this order
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-53b91379bd6e45469467e78f1f057ce7
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353108B2

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