Trifluoroacetic acid → 6-(Bis(4-chlorophenyl)methyl)-4,8-dibromoquinoline

HRID 1778266Notes

Reaction equation

HRID 1778266 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)([C:10]2[CH:11]=[C:12]3[C:17](=[C:18]([Br:20])[CH:19]=2)[N:16]=[CH:15][CH:14]=[C:13]3[Br:21])O)=[CH:4][CH:3]=1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:28][C:25]1[CH:24]=[CH:23][C:22]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:10]2[CH:11]=[C:12]3[C:17](=[C:18]([Br:20])[CH:19]=2)[N:16]=[CH:15][CH:14]=[C:13]3[Br:21])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 118324099Bis(4-chlorophenyl)(4,8-dibromoquinolin-6-yl)methanol

Product 1

HCID 1183239396-(Bis(4-chlorophenyl)methyl)-4,8-dibromoquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To solution of bis(4-chlorophenyl)(4,8-dibromoquinolin-6-yl)methanol (175 mg, 0.325 mmol) and triethylsilane (0.208 mL, 1.3 mmol) in CH2Cl2 was added slowly TFA (0.35 mL, 4.57 mmol). The resulting mixture was stirred for 4 hr at room temperature. The reaction was diluted with CH2Cl2 and washed with Na2CO3 to make the aqueous layer basic. The organics were concentrated and purified by silica column (15% EtOAc/hexanes) chromatography to yield 6-(bis(4-chlorophenyl)methyl)-4,8-dibromoquinoline. (M+H)+: 520, 523, 528.

Workup

  1. washwashed with Na2CO3
  2. concentrationThe organics were concentrated
  3. custompurified by silica column (15% EtOAc/hexanes) chromatography

Sources & evidence

ORD record
ord-ee95233cbe44451f859f57238dae34f7
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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