Diethyl Ether → 2-Bromo-4-(4-chlorophenyl)-4,5,6,7-tetrahydro-1-benzothiophene-4-ol

HRID 1615488노트

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HRID 1615488 반응식
[Br:1][C:2]1[S:3][C:4]2[CH2:10][CH2:9][CH2:8][C:7](=[O:11])[C:5]=2[CH:6]=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([Mg]Br)=[CH:15][CH:14]=1.CCOCC.[NH4+].[Cl-]>CCOC(C)=O.O1CCCC1>[Br:1][C:2]1[S:3][C:4]2[CH2:10][CH2:9][CH2:8][C:7]([C:16]3[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][CH:15]=3)([OH:11])[C:5]=2[CH:6]=1

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 6160702-Bromo-4,5,6,7-tetrahydro-1-benzothiophen-4-oneHCID 178478191HCID 178478191, 화합물

생성물 1

HCID 681832292-Bromo-4-(4-chlorophenyl)-4,5,6,7-tetrahydro-1-benzothiophene-4-ol수율 85%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

In a 250 mL round bottomed flask was placed 2-bromo-6,7-dihydro-1-benzothiophen-4(5H)-one (1.9 g, 8.2 mmol) and tetrahydrofuran (30 mL). To the solution was added 4-chlorophenylmagnesium bromide in ether (1 M, 8.2 mL, 8.2 mmol) and the mixture was stirred for 30 min at rt. To the mixture were added 10% NH4Cl aq (50 mL) and EtOAc (50 mL). The mixture was vigorously stirred for 10 min and then the aqueous phase was discarded. The organic phase was dried over anhydrous MgSO4 and insoluble materials were removed by filtration. The filtrate was concentrated under reduced pressure and the residue was purified pre-packed silica gel (40 g) column chromatography eluted with 0% to 50% EtOAc/hexane to yield the title compound (2.4 g; 85%) as a colorless syrup. 1H NMR (300 MHz, d-chloroform) δ ppm 7.26-7.29 (m, 4H), 6.56 (s, 1H), 2.68-2.86 (m, 2H), 1.81-2.17 (m, 5H).

후처리

  1. customIn a 250 mL round bottomed flask was placed
  2. stirringThe mixture was vigorously stirred for 10 min
  3. dry with materialThe organic phase was dried over anhydrous MgSO4 and insoluble materials
  4. customwere removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified pre-packed silica gel (40 g) column chromatography
  7. washeluted with 0% to 50% EtOAc/hexane

출처 및 근거

ORD 기록
ord-b9225b4d0f2842fd9b4281290f98f8e8
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765746B2

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