Toluene → 7-tert-butyl-3,3-dimethyl-5-thiophen-2-yl-2H-1-benzofuran

HRID 1740887Notes

Reaction equation

HRID 1740887 reaction equation
Br[C:2]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:5]2[O:6][CH2:7][C:8]([CH3:10])([CH3:9])[C:4]=2[CH:3]=1.C([Sn](CCCC)(CCCC)[C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)CCC.C1(C)C=CC=CC=1>CCOCC.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>[C:13]([C:11]1[C:5]2[O:6][CH2:7][C:8]([CH3:10])([CH3:9])[C:4]=2[CH:3]=[C:2]([C:22]2[S:23][CH:24]=[CH:25][CH:26]=2)[CH:12]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 1140TolueneHCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 107793125-Bromo-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzo[b]furan

Product 1

HCID 108507937-tert-butyl-3,3-dimethyl-5-thiophen-2-yl-2H-1-benzofuranYield 281%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 5-bromo-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzo[b]furan (2.26 g, 8.0 mmol), 2-(tributylstannyl)thiophene (3.05 mL, 9.6 mmol), tetrakis(triphenylphosphine)palladium (0.92 g, 0.8 mmol), and 40 mL of toluene is heated under argon at reflux for 2 h. The reaction mixture is cooled to room temperature, diluted with ether, washed with 10% aqueous ammonium hydroxide solution and with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give 6.44 g of a dark oil. Purification by flash column chromatography on silica gel (0.5% ethyl acetate-hexane) yields about 0.98 g (43%) of the title compound initially as a colorless oil, which solidifies upon standing: mp 61-63° C.

Workup

  1. temperatureis heated under argon
  2. temperatureat reflux for 2 h
  3. washwashed with 10% aqueous ammonium hydroxide solution and with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-96e80b6c5d0e40e69e0d7b34c91dc9d3
Source dataset
uspto-grants-1999_10
Patent number
US05972957

Reaction notes

Loading…