Hydrochloric Acid → 2, 3-Difluoro-1-methoxy-4-(4-pentylbicyclo[2.2.2]octyl)benzene

HRID 635144

반응식

HRID 635144 반응식
Br[C:2]12[CH2:9][CH2:8][C:5]([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])([CH2:6][CH2:7]1)[CH2:4][CH2:3]2.[F:15][C:16]1[C:21]([F:22])=[C:20]([O:23][CH3:24])[CH:19]=[CH:18][CH:17]=1.Cl>[N+](C1C=CC=CC=1)([O-])=O.ClCCl.[Fe](Cl)(Cl)Cl>[F:22][C:21]1[C:16]([F:15])=[C:17]([C:2]23[CH2:9][CH2:8][C:5]([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])([CH2:6][CH2:7]2)[CH2:4][CH2:3]3)[CH:18]=[CH:19][C:20]=1[O:23][CH3:24]

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 27693442,3-DifluoroanisoleHCID 125349771-Bromo-4-pentylbicyclo[2.2.2]octane

생성물 1

HCID 540227622, 3-Difluoro-1-methoxy-4-(4-pentylbicyclo[2.2.2]octyl)benzene수율 44%

시약·촉매·용매 3

HCID 24380Iron chloride (FeCl3)촉매HCID 6344Dichloromethane용매HCID 7416Nitrobenzene용매2회

반응 조건

온도
80 °C

실험 절차

A solution of 1-bromo-4-pentylbicyclo[2.2.2]octane (6 g, 23 mmol) in sieve-dried nitrobenzene (100 cm3) is added dropwise to a stirred solution of 2, 3-difluoro-4-methoxybenzene (6 g, 23 mmol) and anhydrous iron(III)chloride (1.2 g, 9 mmol) in sieve-dried nitrobenzene (100 cm3) maintained at 80° C. throughout the addition and overnight. The cooled solution is added to a small volume of hydrochloric acid and stirred for 20 min. The organic layer is separated off and steam-distilled to yield a solid residue. This is taken up in dichloromethane and dried (MgSO4). The raw product is crystallised from ethanol to yield the desired 2, 3-difluoro-1-methoxy-4-(4-pentylbicyclo[2.2.2]octyl)benzene (3.2 g, 44%)

후처리

  1. customThe organic layer is separated off
  2. distillationsteam-distilled
  3. customto yield a solid residue
  4. dry with materialdried (MgSO4)
  5. customThe raw product is crystallised from ethanol

출처 및 근거

ORD 기록
ord-ddc99246cd054390a1b76c96b70ac2c5
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06187393B1

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