Formic Acid → 5-Bromo-3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran

HRID 2290116Notes

Reaction equation

HRID 2290116 reaction equation
Br[C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([CH:9]([CH3:11])[CH3:10])[C:3]=1[O:12][CH2:13][C:14]([CH3:16])=[CH2:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1CCCCC1.C(O)=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O>[Br:8][C:6]1[CH:5]=[C:4]([CH:9]([CH3:11])[CH3:10])[C:3]2[O:12][CH2:13][C:14]([CH3:16])([CH3:15])[C:2]=2[CH:7]=1

Participants

7

Reactant 4

HCID 284Formic AcidHCID 8082PiperidineHCID 11776TriphenylphosphineHCID 154540751,5-Dibromo-3-isopropyl-2-(2-methyl-allyloxy)-benzene2×

Product 1

HCID 154540775-Bromo-3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

Following general procedure C and using 1,5-dibromo-3-isopropyl-2-(2-methyl-allyloxy)-benzene (Compound 6, 28.45 g, 82 mmol), palladium(II)acetate (0.808 g, 3.5 mmol), triphenyl phosphine (1.02 g, 3.5 mmol), 7.7 mL of piperidine and 21 mL of 98% formic acid in a total volume of 1L of anhydrous N,N-dimethylformamide, the title compound was obtained as a colorless oil (1.6 g, 7.3%). 1H NMR (300 MHz, CDCl3): δ 7.12 (d, 1H, J=2.2 Hz), 7.03 (d, 1H, J=2.2 Hz), 4.21 (s, 2H), 3.06 (heptet, 1H, J=6.9 Hz), 1.32 (s, 6H), 1.22 (d, 6H, J=6.9 Hz).

Sources & evidence

ORD record
ord-1d0b1261bbbd432b8321ee21befe1f3b
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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