Bromide ion → Ethyl 4-(4-(4-Chloro-2-fluorophenoxy)phenoxy)pentanoate

HRID 1383189

반응식

HRID 1383189 반응식
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)=[C:4]([F:16])[CH:3]=1.Br[CH:18]([CH3:26])[CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].C(=O)([O-])[O-].[K+].[K+].[Br-].C(=O)([O-])[O-].C1(O)C=CC=CC=1.Cl>CN(C=O)C>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([O:13][CH:18]([CH3:26])[CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:11][CH:12]=2)=[C:4]([F:16])[CH:3]=1

참가 물질

9

반응물 7

HCID 259Bromide ionHCID 313Hydrochloric AcidHCID 996PhenolHCID 11430Potassium CarbonateHCID 19660Carbonate IonHCID 316888Ethyl 4-bromopentanoateHCID 140726804-(4-Chloro-2-fluorophenoxy)phenol

생성물 1

HCID 13880907Ethyl 4-(4-(4-Chloro-2-fluorophenoxy)phenoxy)pentanoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
130 °C

실험 절차

A stirred mixture of 4-(4-chloro-2-fluorophenoxy)phenol (2.3 g, 0.0103 mole), ethyl 4-bromopentanoate (2.01 g, 0.103 mole), and potassium carbonate (1.46 g, 0.105 mole) in DMF (20 ml) was heated in an oil bath at 130° C. for one hour. Additional bromide (0.05 g) and carbonate (0.5 g) were added each hour for the next four hours. At the end of this period, gas chromatography indicated that most of the starting phenol had reacted. After cooling, the reaction mixture was poured into 4N HCl solution (200 ml), and the product extracted into a 1:1 mixture of ether-pentane (2×150 ml). The organic extracts were combined, washed with 10% NaOH solution (200 ml), dried (MgSO4), then the solvent evaporated. The resulting orange oil was purified via preparative HPLC (9:1 hexane/ethyl acetate) with the second peak being collected. Removal of the solvent gave the desired ester as a light yellow oil: RI=1.5344@25° C. Calc: C, 62.21; H, 5.50. Found: C, 62.38; H, 5.33.

후처리

  1. customhad reacted
  2. temperatureAfter cooling
  3. extractionthe product extracted into a 1:1 mixture of ether-pentane (2×150 ml)
  4. washwashed with 10% NaOH solution (200 ml)
  5. dry with materialdried (MgSO4)
  6. customthe solvent evaporated
  7. customThe resulting orange oil was purified via preparative HPLC (9:1 hexane/ethyl acetate) with the second peak
  8. custombeing collected
  9. customRemoval of the solvent

출처 및 근거

ORD 기록
ord-eb8dbfff3b8649bb929c64d354cf6ccd
출처 데이터셋
uspto-grants-1989_02
특허 번호
US04808750

연결된 노트

불러오는 중…