Acetic Acid → 3-Bromo-2-fluoro-6-methoxybenzaldehyde

HRID 1095072노트

반응식

HRID 1095072 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[F:10].C(NC(C)C)(C)C.[Li].CN(C)[CH:21]=[O:22].C(O)(=O)C>O1CCCC1.O>[Br:1][C:2]1[C:3]([F:10])=[C:4]([C:5]([O:8][CH3:9])=[CH:6][CH:7]=1)[CH:21]=[O:22]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 37184441-Bromo-2-fluoro-4-methoxybenzeneHCID 45051747Lithium diisopropylamine

생성물 1

HCID 577432213-Bromo-2-fluoro-6-methoxybenzaldehyde수율 89%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

To a solution of 4-bromo-3-fluoroanisole (10 g, 48.7 mmol, Matrix) in tetrahydrofuran (100 mL) at −78° C. was added lithium diisopropyl amine (32.5 mL, 1.8 M in THF, 58.4 mmol) dropwise during a period of 15 min. The mixture was stirred at −78° C. for another 20 mins. Then N,N-dimethyl-formamide (4.53 mL, 58.4 mmol) was added in one portion. The mixture was stirred at −78° C. for 10 min, then quenched with acetic acid (12 g, 194 mmol) and followed by the addition of water (61 mL). The mixture was partitioned between ethyl acetate and water. The organic layer was separated, concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:4) to give 3-bromo-2-fluoro-6-methoxy-benzaldehyde as a yellow solid (Yield: 10 g, 89%)

후처리

  1. stirringThe mixture was stirred at −78° C. for 10 min
  2. customThe mixture was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography (EtOAc:hexanes=1:4)

출처 및 근거

ORD 기록
ord-f6d740b1e3b34751afb97d2e9fdbdb75
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08134001B2

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