Dichloromethane → 2-(1-Benzofuran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 660721Notes

Reaction equation

HRID 660721 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3](OS(C(F)(F)F)(=O)=O)=[CH:2]1.C(N(CC)CC)C.[CH3:25][C:26]1([CH3:33])[C:30]([CH3:32])([CH3:31])[O:29][BH:28][O:27]1.C(Cl)Cl>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:25][C:26]1([CH3:33])[C:30]([CH3:32])([CH3:31])[O:29][B:28]([C:3]2[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[O:1][CH:2]=2)[O:27]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 21480510Benzo[b]furan-3-yl trifluoromethanesulfonate

Product 1

HCID 438110312-(1-Benzofuran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
150 °C

Procedure

To a solution of trifluoromethanesulfonic acid benzofuran-3-yl ester (half of the amount from step A) in THF is added triethylamine (732 mg, 7.23 mmol), 4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (3.2 mL of a 1.0M in THF, 3.2 mmol) and Pd(dppf)Cl2.CH2Cl2 (76 mg, 0.096 mmol). The mixture is heated at 150° C. under microwave conditions for 3 min. The mixture is filtered and the filtrate evaporated under reduced pressure. The residual oil is purified by flash chromatography using hexane/EtOAc (9:1) as eluent to give the title compound.

Workup

  1. filtrationThe mixture is filtered
  2. customthe filtrate evaporated under reduced pressure
  3. customThe residual oil is purified by flash chromatography

Sources & evidence

ORD record
ord-bff221ed776d4387965f10b2f1c3c138
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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