1-Bromo-3-chloropropane → 2-Chloro-4-(3-chloro-propoxy)-benzaldehyde

HRID 2420971노트

반응식

HRID 2420971 반응식
Br[CH2:2][CH2:3][CH2:4][Cl:5].[Cl:6][C:7]1[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:8]=1[CH:9]=[O:10].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Cl:6][C:7]1[CH:14]=[C:13]([O:15][CH2:2][CH2:3][CH2:4][Cl:5])[CH:12]=[CH:11][C:8]=1[CH:9]=[O:10]

참가 물질

5

반응물 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 1853632-Chloro-4-hydroxybenzaldehyde

생성물 1

HCID 574347552-Chloro-4-(3-chloro-propoxy)-benzaldehyde수율 84.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
65 °C

실험 절차

1-Bromo-3-chloropropane (2.55 g, 16.2 mmol, 1.0 equiv) was added to a solution of 2-chloro-4-hydroxybenzaldehyde (2.54 g, 16.2 mmol) and K2CO3 (4.48 g, 32.4 mmol) in acetonitrile (41 mL). The mixture was heated at 65° C. for 18 h, then cooled to room temperature (rt) and filtered through diatomaceous earth. The filtrate was concentrated to yield the crude product, which was purified by column chromatography (silica gel, 5% EtOAc in hexanes) to afford 3.19 g of a colorless oil (66%). 1H NMR (400 MHz, CD3OD): 10.3 (s, 1H), 7.87 (d, J=8.0, 1H), 7.10 (d, J=4.0, 1H), 7.03 (dd, J=8.0, 4.0, 1H), 4.23 (t, J=8.0, 2H), 3.76 (t, J=8.0, 2H), 2.31-2.22 (m, 2H).

후처리

  1. temperaturecooled to room temperature (rt)
  2. filtrationfiltered through diatomaceous earth
  3. concentrationThe filtrate was concentrated
  4. customto yield the crude product, which
  5. customwas purified by column chromatography (silica gel, 5% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-312364090d3644958e9d920eb3b0a2ba
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07956066B2

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