Trifluoroacetic acid → HCID 178515443, compound

HRID 1778218Notes

Reaction equation

HRID 1778218 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][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]=[C:4]([O:28]C(C)(C)C)[CH:3]=1.[SiH](CC)(CC)CC.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:27][C:24]1[CH:25]=[CH:26][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](=[CH:7][CH:8]=2)[N:5]=[C:4]([OH:28])[CH:3]=[C:2]3[Br:1])=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 118323945(4-Bromo-2-tert-butoxyquinolin-6-yl)bis(4-chlorophenyl)methanol

Product 1

HCID 178515443HCID 178515443, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 100-mL round-bottom flask, was placed a solution of [4-bromo-2-(tert-butoxy)quinolin-6-yl]bis(4-chlorophenyl)methanol (1.5 g, 2.82 mmol, 1.00 equip) in dichloromethane (55 mL), Et3SiH (1.3 g, 4.00 equip), and trifluoroacetic acid (8 g, 70.77 mmol, 25.00 equip). The resulting solution was stirred overnight at room temperature. The pH value of the solution was adjusted to 7-8 with sodium bicarbonate. The resulting solution was extracted with DCM (3×50 ml) and the organic layers combined. The resulting mixture was washed with water (2×50 mL). The resulting mixture was washed with brine (1×50 mL). The resulting mixture was dried over anhydrous sodium sulfate and concentrated to yield 6-[bis(4-chlorophenyl)methyl]-4-bromoquinolin-2-ol as a white solid. (ES, m/z): [M+H]+ 433

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. extractionThe resulting solution was extracted with DCM (3×50 ml)
  3. washThe resulting mixture was washed with water (2×50 mL)
  4. washThe resulting mixture was washed with brine (1×50 mL)
  5. dry with materialThe resulting mixture was dried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-34a1ffa7769a4808b01924bad72f95b2
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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