1-Bromo-4-fluorobenzene → HCID 18679488, compound

HRID 1633656Notes

Reaction equation

HRID 1633656 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.[Br:12][C:13]1[CH:18]=[CH:17][C:16](F)=[CH:15][CH:14]=1.C1OCCOCCOCCOCCOCCOC1.[F-].[K+]>CS(C)=O.O.CCOCC>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([N:8]2[C:9]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)[CH:6]=[CH:7]2)=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 99931-Bromo-4-fluorobenzene2×HCID 138725-MethoxyindoleHCID 2855718-Crown-62×HCID 522689Potassium Fluoride2×

Product 1

HCID 18679488HCID 18679488, compoundYield 84.4%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
120 °C

Procedure

To 14.7 g (0.1 mol) 5-methoxyindole in 100 ml DMSO were added 32.6 ml (0.3 mol) 1-bromo-4-fluorobenzene, 1.06 g (0.04 mol) 18-crown-6 and 10.92 g (60 mmol) KF on alox. The suspension was heated to 120° C. for 48 h. Additional 21.7 ml (0.2 mol) 1-bromo-4-fluorobenzene, 1.06 g (0.04 mol) 18-crown-6 and 10.92 g (60 mmol) KF on alox were added, and the mixture was stirred at 130° C. for 20 h. At RT, ether and water were added, the phases were separated and the inorganic phase was extracted with ether. The combined organic phases were washed with water and dried over Na2SO4. The residue was triturated in ethanol to yield 25.5 g (84%) 1-(4-Bromo-phenyl)-5-methoxy-1H-indole as light brown solid, mp 90-91° C., MS: 301 (M, 1Br).

Workup

  1. customthe phases were separated
  2. extractionthe inorganic phase was extracted with ether
  3. washThe combined organic phases were washed with water
  4. dry with materialdried over Na2SO4
  5. customThe residue was triturated in ethanol

Sources & evidence

ORD record
ord-e4d9d1087d064b708d22f16a3a218aa3
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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