3-Bromo-4-(trifluoromethoxy)benzoic acid → HCID 67211313, compound

HRID 2040532Notes

Reaction equation

HRID 2040532 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][C:12]([F:15])([F:14])[F:13])[C:5]([OH:7])=[O:6].[C:16]([Cu])#[N:17]>CN1CCCC1=O.ClCCl>[C:16]([C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][C:12]([F:15])([F:14])[F:13])[C:5]([OH:7])=[O:6])#[N:17]

Participants

5

Reactant 2

HCID 202740913-Bromo-4-(trifluoromethoxy)benzoic acidHCID 178418546HCID 178418546, compound

Product 1

HCID 67211313HCID 67211313, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
200 °C

Procedure

3-Bromo-4-(trifluoromethoxy)benzoic acid (1.4 g, 4.91 mmol) and cyanocopper (0.572 g, 6.39 mmol) were mixed in N-methyl-2-pyrrolidinone (NMP) (14 mL). The mixture was heated in a microwave at 200° C. for 2 h. The reaction was diluted with dichloromethane (150 mL). Celite® was added and the mixture was stirred vigorously for 10 min. The solids were removed by filtration. The organic layer was washed with water (125 mL) and concentrated. The residue was purified by HPLC to give the title compound as an off-white solid (0.979 g). LCMS m/z=232.3 [M+H]+.

Workup

  1. additionCelite® was added
  2. customThe solids were removed by filtration
  3. washThe organic layer was washed with water (125 mL)
  4. concentrationconcentrated
  5. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-38dcfd3944dd4869a462efdb01082ce5
Source dataset
uspto-grants-2013_11
Patent number
US08580841B2

Reaction notes

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