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

HRID 1615488Notes

Reaction equation

HRID 1615488 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-b9225b4d0f2842fd9b4281290f98f8e8
Source dataset
uspto-grants-2014_07
Patent number
US08765746B2

Reaction notes

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