Dimethylformamide → 4-Chloro-2-fluoro-3-methoxybenzaldehyde

HRID 1912302노트

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HRID 1912302 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([O:9][CH3:10])[C:3]=1[F:11].C([Li])CCC.CN([CH:20]=[O:21])C>C(OCC)C>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([CH:20]=[O:21])=[C:3]([F:11])[C:4]=1[O:9][CH3:10]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 666003671-Bromo-4-chloro-2-fluoro-3-methoxybenzeneHCID 178418339Butyllithium

생성물 1

HCID 579319864-Chloro-2-fluoro-3-methoxybenzaldehyde수율 61%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
-78 °C

실험 절차

1-Bromo-4-chloro-2-fluoro-3-methoxybenzene (23.7 g, 99 mmol, see U.S. Pat. No. 7,300,907 for preparation) was dissolved in dry diethyl ether and cooled to −78° C. 2.5M n-Butyllithium in hexanes (44 mL, 110 mmol) was added in portions, keeping the temperature below −70° C. during the addition. DMF (15.5 mL, 200 mmol) was then added in portions, keeping the temperature below −60° C. The reaction mixture was then allowed to warm to ambient temperature and quenched with water. The organic phase was dried and concentrated. The product was purified by flash chromatography on silica gel (hexane/ethyl acetate gradient) to yield the title compound in sufficient purity for subsequent reactions (11.4 g, 61% yield): 1H NMR (CDCl3) δ 10.32 (s, 1H), 7.55 (m, 1H), 7.3 (m, 1H), 4.05 (d, 3H).

후처리

  1. custom7,300,907 for preparation)
  2. customthe temperature below −70° C.
  3. additionduring the addition
  4. customthe temperature below −60° C
  5. temperatureto warm to ambient temperature
  6. customquenched with water
  7. customThe organic phase was dried
  8. concentrationconcentrated
  9. customThe product was purified by flash chromatography on silica gel (hexane/ethyl acetate gradient)

출처 및 근거

ORD 기록
ord-6582d7d6b2bc4b4e892a853fddac7da1
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609592B2

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