HCID 118324132, compound → HCID 118323941, compound

HRID 1778258Notes

Reaction equation

HRID 1778258 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[C:7]([Br:21])[CH:8]=[C:9]([C:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)=[O:13])[CH:10]=2)[N:5]=[C:4]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:3]=1.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([Mg]Br)=[CH:30][CH:29]=1>O1CCCC1>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([C:12]([C:31]2[CH:32]=[CH:33][C:28]([Cl:27])=[CH:29][CH:30]=2)([C:9]2[CH:10]=[C:11]3[C:6](=[C:7]([Br:21])[CH:8]=2)[N:5]=[C:4]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:3]=[C:2]3[Br:1])[OH:13])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 118324132HCID 118324132, compoundHCID 178478191HCID 178478191, compound

Product 1

HCID 118323941HCID 118323941, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 4,8-dibromo-2-(tert-butoxy)-6-[(4-chlorophenyl)carbonyl]quinoline (440 mg, 0.88 mmol, 1.00 equip) in tetrahydrofuran (30 mL). To the resulting mixture was then added (4-chlorophenyl)magnesium bromide (2.67 mL, 3.00 equip, 1 M) dropwise with stirring at 0° C. The resulting solution was stirred for 3 h at room temperature. The reaction was then quenched by the addition of saturated sodium bicarbonate (50 mL). The resulting solution was extracted with ethyl acetate (100 mL) and the organic layers combined and dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:9) to yield bis(4-chlorophenyl)[4,8-dibromo-2-(tert-butoxy)quinolin-6-yl]methanol as a yellow solid. LCMS (ES, m/z) 610 [M+H]+

Workup

  1. customInto a 100-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. customThe reaction was then quenched by the addition of saturated sodium bicarbonate (50 mL)
  4. extractionThe resulting solution was extracted with ethyl acetate (100 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe solids were filtered out
  7. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-84ec952e6766447c88c7206cc8ec9fad
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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