Boron tribromide → 1-[4-Hydroxy-5-(5,6,7,8-tetrahydronaphthalen-2-yl)thiophen-3-yl]ethanone

HRID 337371Notes

Reaction equation

HRID 337371 reaction equation
C[O:2][C:3]1[C:4]([C:18](=[O:20])[CH3:19])=[CH:5][S:6][C:7]=1[C:8]1[CH:17]=[CH:16][C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[CH:9]=1.B(Br)(Br)Br>C(Cl)(Cl)Cl>[OH:2][C:3]1[C:4]([C:18](=[O:20])[CH3:19])=[CH:5][S:6][C:7]=1[C:8]1[CH:17]=[CH:16][C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[CH:9]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 681622951-[4-Methoxy-5-(5,6,7,8-tetrahydronaphthalen-2-yl)thiophen-3-yl]ethanone

Product 1

HCID 681616421-[4-Hydroxy-5-(5,6,7,8-tetrahydronaphthalen-2-yl)thiophen-3-yl]ethanoneYield 46%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 2.4 g of 1-[4-methoxy-5-(5,6,7,8-tetrahydronaphthalen-2-yl)thiophen-3-yl]ethanone in chloroform (25 ml) cooled with ice, 9.4 ml of boron tribromide (1.0 M dichloromethane solution) was added dropwise, and then the reaction mixture was allowed to react for 1.5 hours. The reaction mixture was poured into 300 ml of ice-cold water and extracted with 250 ml of chloroform. The aqueous layer was extracted with 100 ml of chloroform once, and the extract was combined with the previously chloroform extract, washed with 150 ml of saturated aqueous sodium chloride twice, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue (dark brown oil) was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/20), and the resulting solid was washed with hexane to obtain 1.05 g of the desired product (yield 45%).

Workup

  1. additionwas added dropwise
  2. customto react for 1.5 hours
  3. extractionextracted with 250 ml of chloroform
  4. extractionThe aqueous layer was extracted with 100 ml of chloroform once
  5. extractionextract
  6. washwashed with 150 ml of saturated aqueous sodium chloride twice
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue (dark brown oil) was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/20)
  10. washthe resulting solid was washed with hexane

Sources & evidence

ORD record
ord-ffe43f91657b4d4fafc9c82b0bce043b
Source dataset
uspto-grants-2014_11
Patent number
US08889732B2

Reaction notes

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