m-Chloroperbenzoic acid → 2-(Benzyloxy)-4-fluorophenol

HRID 579795

반응식

HRID 579795 반응식
N(C1C=CC2[O:8]CCOC=2C=1)=C=S.[F:14][C:15]1[CH:20]=[CH:19][C:18](C(=O)C)=[C:17]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:16]=1.ClC1C=C(C(OO)=O)C=CC=1>ClCCl>[F:14][C:15]1[CH:20]=[CH:19][C:18]([OH:8])=[C:17]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:16]=1

참가 물질

5

반응물 3

HCID 70297m-Chloroperbenzoic acidHCID 27761732,3-Dihydro-1,4-benzodioxin-6-yl isothiocyanateHCID 212415771-(2-(Benzyloxy)-4-fluorophenyl)ethanone

생성물 1

HCID 212415852-(Benzyloxy)-4-fluorophenol수율 93%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 11 parts of 1-[4-fluoro-2-(phenylmethoxy)phenyl]ethanone, 8.48 parts of 3-chlorobenzenecarboperoxoic acid and 260 parts of dichloromethane was stirred for 5 days at room temperature. The precipitate was filtered off and the filtrate was stirred in a saturate thiosulfurate solution for 15 minutes. The organic layer was separated and stirred in a saturate hydrogen carbonate solution for 15 minutes. The organic layer was separated, washed with water, dried, filtered and evaporated. The solid residue was stirred in 240 parts of methanol. 5.3 Parts of sodium methoxide were added portionwise. After complete addition, the whole was stirred for 1 hour at room temperature. After evaporation in vacuo at 50° C., the residue was stirred in water and acidified with a hydrochloric acid solution 3N. Trichloromethane was added, the organic layer was separated, washed twice with water, dried, filtered and evaporated, yielding 10 parts (93%) of 4-fluoro-2-(phenylmethoxy)phenol as a residue (intermediate 77).

후처리

  1. filtrationThe precipitate was filtered off
  2. stirringthe filtrate was stirred in a saturate thiosulfurate solution for 15 minutes
  3. customThe organic layer was separated
  4. stirringstirred in a saturate hydrogen carbonate solution for 15 minutes
  5. customThe organic layer was separated
  6. washwashed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. stirringThe solid residue was stirred in 240 parts of methanol
  11. addition5.3 Parts of sodium methoxide were added portionwise
  12. additionAfter complete addition
  13. stirringthe whole was stirred for 1 hour at room temperature
  14. customAfter evaporation in vacuo at 50° C.
  15. stirringthe residue was stirred in water
  16. additionTrichloromethane was added
  17. customthe organic layer was separated
  18. washwashed twice with water
  19. customdried
  20. filtrationfiltered
  21. customevaporated

출처 및 근거

ORD 기록
ord-c1901a0ee32e49fea7b53722cf5f2cf7
출처 데이터셋
uspto-grants-1988_06
특허 번호
US04749702

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