Benzyl Bromide → HCID 68431646, compound

HRID 889280Notes

Reaction equation

HRID 889280 reaction equation
[Br:1][C:2]1[C:3](O)=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([Br:12])=[C:7]([OH:13])[CH:6]=2.[C:15]([O-:18])([O-])=O.[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C>[CH2:21]([O:13][C:7]1[C:8]([Br:12])=[CH:9][C:10]2[C:5](=[CH:4][C:3]([O:18][CH2:15][C:2]3[CH:3]=[CH:4][CH:5]=[CH:10][CH:11]=3)=[C:2]([Br:1])[CH:11]=2)[CH:6]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27951483,6-dibromonaphthalene-2,7-diol

Product 1

HCID 68431646HCID 68431646, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,6-dibromonaphthalene-2,7-diol (67.64 g, 212.7 mmol) in DMF (400 mL) is added K2CO3 (64.7 g, 468.0 mmol). Benzylbromide (56.0 mL, 468 mmol) is added to the reaction (slight exotherm) and the mixture is stirred at RT for 2 days. The solid is filtered washing with 1:4 DMF/H2O and set aside for further extraction. The filtrate is extracted 3× with EtOAc and washed with brine. The EtOAc extracts are concentrated under reduced pressure, dissolved in minimum methylene chloride and triturated into hexanes to give product. The filtered solids are washed with hexanes to give additional material which is combined with the triturated solid to give the title compound.

Workup

  1. filtrationThe solid is filtered
  2. washwashing with 1:4 DMF/H2O
  3. extractionset aside for further extraction
  4. extractionThe filtrate is extracted 3× with EtOAc
  5. washwashed with brine
  6. concentrationThe EtOAc extracts are concentrated under reduced pressure
  7. dissolutiondissolved in minimum methylene chloride
  8. customtriturated into hexanes
  9. customto give product
  10. washThe filtered solids are washed with hexanes
  11. customto give additional material which

Sources & evidence

ORD record
ord-86c715a4122348f0b062b8757878b5d9
Source dataset
uspto-grants-2012_08
Patent number
US08252820B2

Reaction notes

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