Sodium Iodide → Benzyl 3-chloro-5-(3-hydroxypropoxy)benzoate

HRID 1698859노트

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HRID 1698859 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([OH:18])[CH:17]=1)[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:26][CH2:27][CH2:28][OH:29].[I-].[Na+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([O:18][CH2:26][CH2:27][CH2:28][OH:29])[CH:17]=1)[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 10796Cesium carbonate3회HCID 123083-Bromo-1-propanol2회HCID 18322181Benzyl 3-chloro-5-hydroxybenzoate

생성물 1

HCID 18322176Benzyl 3-chloro-5-(3-hydroxypropoxy)benzoate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
50 °C

실험 절차

To a solution of phenol 25 (8.80 g, 33.0 mmol) and 3-bromno-1-propanol (2.9 mL, 33 mmol) in acetonitrile (300 nL) was added solid cesium carbonate (12 g, 37 mmol). After stirring 16hrs at 50° C., more 3-bromo-1-propanol (3.3 mmol) and cesium carbonate (3.3 mmol) were added and the reaction stirred another 2 hrs. After adding more 3-bromo-1-propanol and cesium carbonate (3.3 mmol each) and sodium iodide (3.3 mmol), the reaction was stirred 30 minutes at 65° C., then cooled and filtered. The filtrate was evaporated in vacuo, the residue dissolved in ethyl acetate, washed with water, and the organic layer dried over Na2SO4 and filtered. The evaporated filtrate then gave product 26 (5.96 g 56%). 1H NMR (300 MHz, CDCl3) δ 7.63 (t, 1H, J=1.5 Hz), 7.48 (dd, 1H, J=2.4 Hz, 1.4 Hz), 7.46-7.31 (m, 5H), 7.09 (t, 1H, J=2.4 Hz), 5.35 (s, 2H), 4.14 (t, 2H, J =6.0 Hz), 3.85 (t, 2H, J=6.0 Hz), 2.05 (pentet, 2H, J=6.0 Hz).

후처리

  1. stirringthe reaction stirred another 2 hrs
  2. stirringthe reaction was stirred 30 minutes at 65° C.
  3. temperaturecooled
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. dissolutionthe residue dissolved in ethyl acetate
  7. washwashed with water
  8. dry with materialthe organic layer dried over Na2SO4
  9. filtrationfiltered

출처 및 근거

ORD 기록
ord-1296ac4b59674eb2b02118fe501f2986
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06344466B2

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