Water → HCID 2238016, compound

HRID 1644138Notes

Reaction equation

HRID 1644138 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10].[I-].[Na+].Br[CH2:14][CH2:15][CH2:16][Br:17].[OH2:18]>CN(C=O)C.C(O)C>[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:6][CH2:7][CH2:8][O:18][C:5]1[CH:4]=[CH:9][CH:14]=[CH:15][C:16]=1[Br:17]

Participants

8

Reactant 5

HCID 962WaterHCID 5238Sodium IodideHCID 72442-BromophenolHCID 80011,3-DibromopropaneHCID 24758Sodium hydride

Product 1

HCID 2238016HCID 2238016, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent2×

Procedure

2.6 g (110 mmol) of sodium hydride are added in portions with vigorous stirring to a solution of 18.2 g (105 mmol) of 2-bromophenol in 200 ml of DMF. After the mixture has been stirred for a further 15 min., 1.5 g (10 mmol) of sodium iodide are added. A mixture of 4.8 ml (50 mmol) of 1,3-dibromopropane in 50 ml of DMF is added dropwise to this mixture, which is subsequently stirred at room temperature for 60 h. 5 ml of ethanol are added dropwise to the reaction mixture, which is then poured into 1000 ml of water and extracted three times with 200 ml of dichloromethane. The combined organic phases are washed five times with 500 ml of water, dried over MgSO4 and evaporated under reduced pressure. The foam which remains is washed by stirring with 200 ml of n-heptane, filtered off with suction, washed with n-heptane and dried under reduced pressure. Yield: 15.0 g, 77.7% of theory, purity: 98.0% according to 1H-NMR.

Workup

  1. additionis added dropwise to this mixture, which
  2. stirringis subsequently stirred at room temperature for 60 h
  3. extractionextracted three times with 200 ml of dichloromethane
  4. washThe combined organic phases are washed five times with 500 ml of water
  5. dry with materialdried over MgSO4
  6. customevaporated under reduced pressure
  7. washThe foam which remains is washed
  8. stirringby stirring with 200 ml of n-heptane
  9. filtrationfiltered off with suction
  10. washwashed with n-heptane
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-8cb003e6829545d79e57090b001cc4a0
Source dataset
uspto-grants-2012_02
Patent number
US08124249B2

Reaction notes

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