Ethyl Acetate → 1-(Bromomethyl)-2-fluoro-4-nitrobenzene

HRID 499201Notes

Reaction equation

HRID 499201 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH3:11].[Br:12]([O-])(=O)=O.[Na+].CCOC(C)=O.S(=O)(O)[O-].[Na+]>O>[Br:12][CH2:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[F:1]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 740252-Fluoro-4-nitrotolueneHCID 23665763Sodium Bisulfite2×HCID 23668195Sodium Bromate

Product 1

HCID 218861321-(Bromomethyl)-2-fluoro-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-Fluoro-1-methyl-4-nitro-benzene (1 g, 6.45 mmol) and sodium bromate (2.92 g, 19.33 mmol) in an EtOAc:water (12 mL:9 mL) mixture, is added dropwise via addition funnel a 3.85M solution of sodium bisulfite 5.20 mL, 19.33 mmol). The mixture is vigorously stirred for six days and then sodium bisulfite (10 mL) is added and organic layer separated and washed with aqueous saturated solution of sodium bicarbonate. The organic phase is dried with magnesium sulfate, filtered and evaporated at reduced pressure to afford a mixture of title compound and starting 2-fluoro-1-methyl-4-nitro-benzene in a 5:1 ratio (1H-NMR) which is used in the next step without further purification. ES+(m/z) 235 [M+H]).

Workup

  1. customorganic layer separated
  2. washwashed with aqueous saturated solution of sodium bicarbonate
  3. dry with materialThe organic phase is dried with magnesium sulfate
  4. filtrationfiltered
  5. customevaporated at reduced pressure
  6. customto afford

Sources & evidence

ORD record
ord-b41892aa70564ec396ad3593d85134ab
Source dataset
uspto-grants-2010_08
Patent number
US07767674B2

Reaction notes

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