Benzyl Bromide → HCID 10988792, compound

HRID 2306176Notes

Reaction equation

HRID 2306176 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([O:9][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 115713,5-Dichlorophenol

Product 1

HCID 10988792HCID 10988792, compound

Conditions

Temperature
45 °C

Procedure

To a stirred mixture of 3,5-dichlorophenol (3.00 g, 18.4 mmol) and Cs2CO3 (12.0 g, 36.8 mmol) in dry, degassed DMF (150 mL) was added benzyl bromide (3.46 g, 20.2 mmol) dropwise. The reaction mixture was heated to 45° C. for 18 hours, then the solvent was removed under reduced pressure. The residue was partitioned between saturated aqueous NaHCO3 (75 mL) and CH2Cl2 (100 mL). The aqueous layer was extracted further with CH2Cl2 (25 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica, eluting with hexane—2% EtOAc to yield the desired product as a colorless oil.

Workup

  1. customin dry
  2. customdegassed DMF (150 mL)
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was partitioned between saturated aqueous NaHCO3 (75 mL) and CH2Cl2 (100 mL)
  5. extractionThe aqueous layer was extracted further with CH2Cl2 (25 mL)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by flash column chromatography on silica
  10. washeluting with hexane—2% EtOAc

Sources & evidence

ORD record
ord-fc9b5a3b0da04130a0ceea6e90630175
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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