Trifluoroacetic acid → HCID 118324072, compound

HRID 1778272Notes

Reaction equation

HRID 1778272 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[C:7]([O:28][CH3:29])[CH:8]=[C:9]([C:12]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)O)[CH:10]=2)[N:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([CH:12]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[C:9]2[CH:10]=[C:11]3[C:6](=[C:7]([O:28][CH3:29])[CH:8]=2)[N:5]=[CH:4][CH:3]=[C:2]3[Br:1])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 118324107HCID 118324107, compound

Product 1

HCID 118324072HCID 118324072, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

Into a 500-mL 3-necked round-bottom flask, was placed (4-bromo-8-methoxyquinolin-6-yl)bis(4-chlorophenyl)methanol (6 g, 12.27 mmol, 1.00 equip), dichloromethane (200 mL), triethylsilane (8 mL), and trifluoroacetic acid (24 mL). The resulting solution was stirred overnight at 25° C. The resulting solution was diluted with DCM (100 mL). The resulting mixture was washed with saturated sodium bicarbonate (3×100 mL) and dried over anhydrous sodium sulfate. The solids were filtered out. The residue was applied onto a silica gel column with ethyl acetate:petroleum ether (1:1) to yield 6-[bis(4-chlorophenyl)methyl]-4-bromo-8-methoxyquinoline as a yellow solid. LCMS (ES, m/z) 474 [M+H]+

Workup

  1. customInto a 500-mL 3-necked round-bottom flask, was placed
  2. washThe resulting mixture was washed with saturated sodium bicarbonate (3×100 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe solids were filtered out

Sources & evidence

ORD record
ord-cee5178860a04e20b3719828f9b9fc6c
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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