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

HRID 2420971ノート

反応式

HRID 2420971 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
65 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-312364090d3644958e9d920eb3b0a2ba
出典データセット
uspto-grants-2011_06
特許番号
US07956066B2

反応ノート

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