Trifluoroacetic acid → HCID 67518202, compound

HRID 2173190Notes

Reaction equation

HRID 2173190 reaction equation
[Br:1][C:2]1[C:3]([Cl:10])=[C:4]([CH2:8][OH:9])[CH:5]=[CH:6][CH:7]=1.FC(F)(F)[C:13]([O-])=[O:14].[Tl+].C(O)(C(F)(F)F)=O.[O-2].[Mg+2].[Cl-].[Li+]>C(Cl)Cl.[Pd](Cl)Cl.C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:13](=[O:14])[O:9][CH2:8][C:4]=2[C:3]=1[Cl:10]

Participants

9

Reactant 5

HCID 6422Trifluoroacetic acidHCID 433294Lithium ChlorideHCID 6850729Magnesium monoxideHCID 21902506Thallium(1+);2,2,2-trifluoroacetateHCID 67146654(3-Bromo-2-chlorophenyl)methanol

Product 1

HCID 67518202HCID 67518202, compound

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a flask charged with (3-bromo-2-chlorophenyl)methanol (1.1 g, 4.8 mmol) and a stir bar was added thallium trifluoroacetate (2.9 g, 5.3 mmol) and TFA (6 mL). The mixture was allowed to stir at RT for 16 hours. The volatiles were removed under reduced pressure. The residue was pumped under high vacuum for 15 minutes before palladium (II) chloride (0.085 g, 0.48 mmol), magnesium oxide (0.39 g, 9.6 mmol), lithium chloride (0.20 g, 4.8 mmol), and ethanol (30 mL) were added. The mixture was stirred under an atmosphere of carbon mono-oxide until the reaction turned black. The reaction was diluted with DCM. The suspension was filtered through a pad of Celite® to remove the solids. The filtrate was adsorbed onto silica gel, and purified by MPLC to afford 5-bromo-4-chloro-2-benzofuran-1(3H)-one. LC-MS (IE, m/z): 249 [M+1]+;

Workup

  1. customThe volatiles were removed under reduced pressure
  2. additionwere added
  3. stirringThe mixture was stirred under an atmosphere of carbon mono-oxide until the reaction
  4. filtrationThe suspension was filtered through a pad of Celite®
  5. customto remove the solids
  6. custompurified by MPLC

Sources & evidence

ORD record
ord-00da9699a761495db6d99b3af889fd76
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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