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

HRID 1095076노트

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HRID 1095076 반응식
[Cl: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>[Cl: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 27245211-Chloro-2-fluoro-4-methoxybenzeneHCID 45051747Lithium diisopropylamine

생성물 1

HCID 221397073-Chloro-2-fluoro-6-methoxybenzaldehyde수율 85%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

To a solution of 4-chloro-3-fluoroanisole (10.2 g, 63.5 mmol, Oakwood) in tetrahydrofuran (100 mL) at −78° C. was added lithium diisopropyl amine (42.3 mL, 1.8 M in THF, 76.2 mmol) dropwise during a period of 15 min. The mixture was stirred at −78° C. for another 20 mins. Then N,N-dimethyl-formamide (5.9 mL, 76.2 mmol) was added in one portion. The mixture was stirred at −78° C. for 10 min, then quenched with acetic acid (15.6 g, 254 mmol) and followed by the addition of water (80 mL). The mixture was partitioned between ethyl acetate and water. The organic layer was separated, concentrated to give 3-chloro-2-fluoro-6-methoxy-benzaldehyde as a yellow solid (Yield: 10 g, 85%)

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

출처 및 근거

ORD 기록
ord-48e648302af648bd8c1c2e8bed33d01d
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08134001B2

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