p-Toluenesulfonic acid → 2-(4-Bromo-2-chlorophenoxy)methyl-8-phenethyl-1,4-dioxa-8-azaspiro[4,5]decane

HRID 77336

반응식

HRID 77336 반응식
[OH:1][CH2:2][CH:3]1[CH2:7][O:6][C:5]2([CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:9][CH2:8]2)[O:4]1.[Cl:21][C:22]1[CH:27]=[C:26]([Br:28])[CH:25]=[CH:24][C:23]=1O.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:28][C:26]1[CH:25]=[CH:24][C:23]([O:1][CH2:2][CH:3]2[CH2:7][O:6][C:5]3([CH2:8][CH2:9][N:10]([CH2:13][CH2:14][C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH2:11][CH2:12]3)[O:4]2)=[C:22]([Cl:21])[CH:27]=1

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 198594-Bromo-2-chlorophenolHCID 667015182-Hydroxymethyl-8-phenethyl-1,4-dioxa-8-azaspiro[4,5]decane2회

생성물 1

HCID 510309912-(4-Bromo-2-chlorophenoxy)methyl-8-phenethyl-1,4-dioxa-8-azaspiro[4,5]decane수율 95%

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

2-hydroxymethyl-8-phenethyl-1,4-dioxa-8-azaspiro[4,5]decane (compound 1, 50 gm, 0.18 mole) was dissolved in toluene (300 ml) at room temperature. To this 44 gms of 2-chloro-4-bromophenol in toluene (150 ml) was added at room temperature 28° C. in the presence of ParaToluenesulfonic Acid (PTSA, 3.5 gm). Reaction mixture was refluxed with stirring for 13 hrs. It was then cooled and filtered. The filtrate was given water wash to bring the pH to neutral. Toluene was removed under vacuum to obtain a thick brick red colored product 95% yield.

후처리

  1. customReaction mixture
  2. temperaturewas refluxed
  3. temperatureIt was then cooled
  4. filtrationfiltered
  5. washwash
  6. customToluene was removed under vacuum

출처 및 근거

ORD 기록
ord-0b06f1d871e44007ad9e616efa9e2839
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841296B2

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