Sodium Carbonate → 2-(3-Thiophen-3-yl-phenyl)-ethanol

HRID 1713672Notes

Reaction equation

HRID 1713672 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][CH2:6][OH:7].[S:11]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12]1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[S:11]1[CH:15]=[CH:14][C:13]([C:2]2[CH:3]=[C:4]([CH2:5][CH2:6][OH:7])[CH:8]=[CH:9][CH:10]=2)=[CH:12]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 581760Thiophene-3-boronic acidHCID 27340902-(3-Bromophenyl)ethan-1-ol

Product 1

HCID 199171332-(3-Thiophen-3-yl-phenyl)-ethanol

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 3-bromo-phenethyl-alcohol (1 g, 4.97 mmol), 3-thiophene-boronic-acid (1.9 g, 14.9 mmol, 3.0 equiv), Pd(PPh3)4 (172 mg, 0.149 mmol, 0.03 equiv), and 2M Na2CO3 (10.8 mL, 22.4 mmol, 4.5 equiv) in toluene (40 mL) is heated to reflux 1 h, under an argon atmosphere. The resulting suspension is allowed to cool to RT and filtered through a pad of celite, washing the filter cake with CH2Cl2 and water. The layers are separated. The organic phase is washed with brine, dried (Na2SO4), filtered and concentrated. Purification of the crude material by silica gel column chromatography (CH2Cl2/Et2O, 95/5) affords the title compound: ES-MS: 205.0 [M+H]+; single peak at tR=4.27 min (System 2); Rf=0.32 (CH2Cl2/Et2O, 95/5).

Workup

  1. temperatureis heated
  2. temperatureto reflux 1 h, under an argon atmosphere
  3. filtrationfiltered through a pad of celite
  4. washwashing the filter cake with CH2Cl2 and water
  5. customThe layers are separated
  6. washThe organic phase is washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification of the crude material by silica gel column chromatography (CH2Cl2/Et2O, 95/5)

Sources & evidence

ORD record
ord-c333d8530e324d0e887d6deebcdbac7a
Source dataset
uspto-grants-2010_09
Patent number
US07795288B2

Reaction notes

Loading…