Benzyl Bromide → HCID 17985978, compound

HRID 2054542Notes

Reaction equation

HRID 2054542 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6].C(=O)(O)[O-].[Na+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([O:7][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:6]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 2306533-Fluoro-4-nitrobenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 17985978HCID 17985978, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 3-fluoro-4-nitroberizoic acid (33.0 g) in anhydrous DMF (300 ml) was cooled to 0° C., treated with sodium bicarbonate (13.5 g) and stirred for 30 min. The mixture was treated dropwise with benzyl bromide (19.0 ml) stirred for a further 30 min then allowed to warm to room temperature while stirring overnight (18 h). The resulting orange solution was evaporated under reduced pressure and the residue partitioned between ethyl acetate (1200 ml) and saturated aqueous sodium carbonate (1600 ml). The organic layer was split into 2×600 ml portions and each was washed with water (2×500 ml), brine (200 ml), dried over anhydrous magnesium sulfate then filtered. The filtrates were combined and evaporated under reduced pressure to give the title compound (38.2 g) as an orange oil which crystallised on standing overnight.

Workup

  1. stirringstirred for a further 30 min
  2. temperatureto warm to room temperature
  3. stirringwhile stirring overnight (18 h)
  4. customThe resulting orange solution was evaporated under reduced pressure
  5. customthe residue partitioned between ethyl acetate (1200 ml) and saturated aqueous sodium carbonate (1600 ml)
  6. customThe organic layer was split into 2×600 ml portions
  7. washeach was washed with water (2×500 ml), brine (200 ml)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationthen filtered
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5572010ea9684eba983c9ff628073f40
Source dataset
uspto-grants-2008_02
Patent number
US07329685B2

Reaction notes

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