5-Bromo-1-benzothiophene → 5-Benzylbenzothiophene

HRID 2075167Notes

Reaction equation

HRID 2075167 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.[Br-].[CH2:12]([Zn+])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1.C(OCC)(=O)C.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH2:12]([C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[CH:7][C:6]=2[CH:10]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 2

HCID 27765785-Bromo-1-benzothiopheneHCID 178419772HCID 178419772, compound

Product 1

HCID 109771175-BenzylbenzothiopheneYield 65%

Reagents, catalysts & solvents 3

HCID 178418851HCID 178418851, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

5-Bromobenzothiophene (2.13 g, 10 mmol) was dissolved in a THF solution of benzyl zinc(II) bromide (0.5M, 10 mL, 20 mmol) in a microwave reaction tube. Pd(PtBu3)2 (255 mg, 0.5 mmol) was added to this solution. The mixture was purged with N2 gas for 3-5 minutes and heated at 100° C. for 30 minutes under microwave irradiation. Upon completion of the reaction, the reaction mixture was diluted with ethyl acetate (150 mL), washed with 1N HCl aqueous solution, brine, filtered through Celite. The filtrate was dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography (ISCO system, 5% EtOAc in hexanes) to give the desired product (65% yield): 1H NMR (400 MHz, CDCl3) δ 7.79 (d, J=8.4 Hz, 1H), 7.63 (s, 1H), 7.40 (d, J=5.6 Hz, 1H), 7.18-7.30 (m, 7H), 4.10 (s, 2H).

Workup

  1. customThe mixture was purged with N2 gas for 3-5 minutes
  2. customUpon completion of the reaction
  3. washwashed with 1N HCl aqueous solution, brine
  4. filtrationfiltered through Celite
  5. dry with materialThe filtrate was dried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (ISCO system, 5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4b53367ea5fa494ea05d488de47d9c7c
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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