Benzyl Bromide → HCID 67244145, compound

HRID 2423240Notes

Reaction equation

HRID 2423240 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[F:7][C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([N+:17]([O-:19])=[O:18])[CH:16]=1)[C:11]([OH:13])=[O:12].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C>[F:7][C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([N+:17]([O-:19])=[O:18])[CH:16]=1)[C:11]([O:13][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:12]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 27590473-Fluoro-5-nitrobenzoic acid

Product 1

HCID 67244145HCID 67244145, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At 10° C., cesium carbonate (5.81 g) was added to a DMF (30 mL) solution of 3-fluoro-5-nitrobenzoic acid (2.20 g), followed by stirring for 30 minutes. Then, benzyl bromide (2.07 g) was dropwise added with taking 30 minutes, and then followed by further stirring for 10 minutes. The insoluble matter was separated by filtration, followed by evaporation under reduced pressure. This was subjected to liquid-liquid separation with ether and water added thereto, and the organic layer was dried and then evaporated to obtain benzyl 3-fluoro-5-nitrobenzoate (3.11 g). EI: 275.

Workup

  1. waitwith taking 30 minutes
  2. stirringby further stirring for 10 minutes
  3. customThe insoluble matter was separated by filtration
  4. customfollowed by evaporation under reduced pressure
  5. customThis was subjected to liquid-liquid separation with ether and water
  6. additionadded
  7. customthe organic layer was dried
  8. customevaporated

Sources & evidence

ORD record
ord-af63057fb5ba483fb73bcce7bd3624d2
Source dataset
uspto-grants-2011_06
Patent number
US07960562B2

Reaction notes

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