Methyl 4,8-dibromoquinoline-6-carboxylate → Bis(4-chlorophenyl)(4,8-dibromoquinolin-6-yl)methanol

HRID 1778265Notes

Reaction equation

HRID 1778265 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.[Br:10][C:11]1[C:20]2[C:15](=[C:16]([Br:25])[CH:17]=[C:18]([C:21]([O:23]C)=O)[CH:19]=2)[N:14]=[CH:13][CH:12]=1>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:21]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)([C:18]2[CH:19]=[C:20]3[C:15](=[C:16]([Br:25])[CH:17]=2)[N:14]=[CH:13][CH:12]=[C:11]3[Br:10])[OH:23])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 118324078Methyl 4,8-dibromoquinoline-6-carboxylateHCID 178478191HCID 178478191, compound

Product 1

HCID 118324099Bis(4-chlorophenyl)(4,8-dibromoquinolin-6-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (4-chlorophenyl)magnesium bromide (2.02 mL, 1.0 M in THF) was dropwise added to a suspension of methyl 4,8-dibromoquinoline-6-carboxylate (0.2 g, 0.58 mmol) in THF (5 mL) at room temperature. The resulting mixture was slowly dissolved and became a clear solution after 30 min. During this period of time, cooling was needed, when the temperature of the reaction mixture rose above room temperature. After 2 hr, the reaction was quenched with ice water and saturated NH4Cl followed by EtOAc. The aqueous layer was extracted with EtOAc. The combined organics were concentrated and purified by silica column (25-30% EtOAc/hexanes) chromatography to yield bis(4-chlorophenyl)(4,8-dibromoquinolin-6-yl)methanol. (M+H)+: 536, 540, 541

Workup

  1. dissolutionThe resulting mixture was slowly dissolved
  2. customafter 30 min
  3. waitDuring this period of time
  4. temperaturecooling
  5. customrose above room temperature
  6. customthe reaction was quenched with ice water and saturated NH4Cl
  7. extractionThe aqueous layer was extracted with EtOAc
  8. concentrationThe combined organics were concentrated
  9. custompurified by silica column (25-30% EtOAc/hexanes) chromatography

Sources & evidence

ORD record
ord-d2ecffc3a3c544d0999760b4fd0e15bb
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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