Sulfuric Acid → 1-[Bis(4-fluorophenyl)methoxy]-4-chlorobutane

HRID 1619726

반응식

HRID 1619726 반응식
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6].S(=O)(=O)(O)O.[F:12][C:13]1[CH:27]=[CH:26][C:16]([CH:17](O)[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[F:12][C:13]1[CH:14]=[CH:15][C:16]([CH:17]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[O:6][CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])=[CH:26][CH:27]=1

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 135694-Chloro-1-butanolHCID 1230494,4'-Difluorobenzhydryl alcohol

생성물 1

HCID 107573721-[Bis(4-fluorophenyl)methoxy]-4-chlorobutane수율 75%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of 4-chloro-1-butanol (6.51 g, 60 mmol), 1 mL of concentrated sulfuric acid and 4,4′-difluorobenzhydrol (2.2 g, 10 mmol) in 50 mL of toluene was heated at reflux for 12 h. The reaction mixture was cooled, washed successively with saturated sodium bicarbonate solution (50 mL) and water (50 mL). The organic layer was dried over MgSO4, filtered and the solvent was removed by rotary evaporation. The resultant brown oil was purified on a silica gel column. Elution with 2% ethyl acetate/hexane afforded 2.33 g (7.5 mmol, 75%) of the product as a colorless oil. 1H NMR (CDCl3): δ 1.71-1.80 (2H, m), 1.84-1.93 (2H, m), 3.43 (2H, t, J=6.0), 3.52 (2H, t, J=6.4), 5.30 (1H, s) 6.95-7.02 (4H, m), 7.24-7.29 (4H, m)

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 12 h
  3. temperatureThe reaction mixture was cooled
  4. washwashed successively with saturated sodium bicarbonate solution (50 mL) and water (50 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent was removed by rotary evaporation
  8. customThe resultant brown oil was purified on a silica gel column
  9. washElution with 2% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-16b3a2696f5f4829a67fa7fcb42a0509
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772319B2

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