Ethyl Acetate → HCID 66643951, compound

HRID 1474323Notes

Reaction equation

HRID 1474323 reaction equation
[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([CH2:9][OH:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[Li+].[Cl-].C[CH2:15][O:16]C(C)=O>FC(F)(F)C(O)=O.CO.Cl[Pd]Cl>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]2[C:15](=[O:16])[O:10][CH2:9][C:4]=2[C:3]=1[CH3:11]

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 433294Lithium ChlorideHCID 10656303(3-bromo-2,5-dimethylphenyl)methanol

Product 1

HCID 66643951HCID 66643951, compound

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 887MethanolSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of (3-bromo-2,5-dimethylphenyl)methanol (1.6 g, 7.4 mmol) in trifluoroacetic acid (20 mL) was added Tl(OOCF3)3 (4 g, 7.4 mmol) at r.t, then the reaction was stirred at r.t overnight under N2. The mixture was concentrated under pressure. The residue solids, LiCl (0.6 g, 14.9 mmol), MgO (0.6 g, 14.9 mmol) and PdCl2 (0.13 g, 0.74 mmol) in MeOH were stirred under CO at 1 Mpa over night. EtOAc was added to the mixture and filtered. The organic phase was concentrated to afford 5-bromo-4,7-dimethyl-2-benzofuran-1(3H)-one.

Workup

  1. concentrationThe mixture was concentrated under pressure
  2. filtrationfiltered
  3. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-20e688a2251a46489fcd3c1460248650
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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