Bromine → HCID 15347207, compound

HRID 1939965Notes

Reaction equation

HRID 1939965 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH2:19][CH2:20]O)[CH:16]=[CH:17][CH:18]=1.[Br:22]Br>C(Cl)Cl>[Br:22][CH2:20][CH2:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([O:12][CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)[CH:14]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 15347206HCID 15347206, compound

Product 1

HCID 15347207HCID 15347207, compoundYield 189.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

8.6 g of 2-[3-(quinol-2-ylmethoxy)phenyl]ethanol are dissolved in 200 ml of methylene chloride. There are added 9.8 g of tdphenylphosphine and then, at 10° C., 1.9 g of bromine dissolved in 50 ml of methylene chloride. Stirring is carded out at room temperature for 16 hours. The mixture is concentrated to dryness and the residue is taken up in ether. The mixture is washed with a 10% sodium carbonate solution and dried over sodium sulphate. Concentration to dryness is carded out. The residue is chromatographed on 450 g of silica using methylene chloride as eluant. There are obtained 7.7 g of 1-bromo-2-[3-(quinol-2-yl-methoxy) phenyl]ethane. Yield: 72%.

Workup

  1. additionThere are added 9.8 g of tdphenylphosphine
  2. concentrationThe mixture is concentrated to dryness
  3. washThe mixture is washed with a 10% sodium carbonate solution
  4. dry with materialdried over sodium sulphate
  5. concentrationConcentration to dryness
  6. customThe residue is chromatographed on 450 g of silica

Sources & evidence

ORD record
ord-407e52a38f9d4762809746e00ccb04e1
Source dataset
uspto-grants-1997_12
Patent number
US05698567

Reaction notes

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