3-Fluorobenzyl bromide → HCID 23226992, compound

HRID 1956173Notes

Reaction equation

HRID 1956173 reaction equation
[SH:1][C:2]1[C:7]([CH:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][C:9]2([CH3:18])[CH3:17])=[CH:6][N:5]=[CH:4][N:3]=1.[F:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23]Br.C(=O)([O-])[O-].[NH4+].[NH4+]>C(#N)C>[F:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][S:1][C:2]1[C:7]([CH:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][C:9]2([CH3:18])[CH3:17])=[CH:6][N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 680073-Fluorobenzyl bromideHCID 517111Ammonium CarbonateHCID 178422611HCID 178422611, compound

Product 1

HCID 23226992HCID 23226992, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.57 g (0.002 mol) of 4-mercapto-5-(2,2-dimethylindan-1-yl)pyrimidine, 0.57 g (0.003 mol) of 3-fluorobenzyl bromide, and 0.41 g (0.003 mol) in 10 mL of acetonitrile was stirred at ambient temperature for 2 hr. Saturated aqueous ammonium carbonate (5 mL) was added and the mixture obtained was extracted with ethyl acetate. The extract solution was washed with water and with concentrated aqueous sodium chloride and then was dried over sodium sulfate and concentrated by evaporation under reduced pressure. The resulting oil was low pressure liquid chromatographed on silica gel eluting first with hexane and then with a 20:80 by volume mixture of ethyl acetate and hexane. The eluent fractions containing the major component were concentrated by evaporation under reduced pressure to obtain the title compound as a white solid melting at 60°-62° C.

Workup

  1. customthe mixture obtained
  2. extractionwas extracted with ethyl acetate
  3. washThe extract solution was washed with water and with concentrated aqueous sodium chloride
  4. dry with materialwas dried over sodium sulfate
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customchromatographed on silica gel eluting first with hexane
  7. additionwith a 20:80 by volume mixture of ethyl acetate and hexane
  8. additionThe eluent fractions containing the major component
  9. concentrationwere concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-9e74268ea6294dd695862118decfbd08
Source dataset
uspto-grants-1998_07
Patent number
US05780465

Reaction notes

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