Sodium Dithionite → 4-Bromo-5-fluoro-2-methoxyaniline

HRID 897777Notes

Reaction equation

HRID 897777 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[Br:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([N+:18]([O-])=O)=[CH:12][C:11]=1[F:21]>C(O)C.O>[Br:9][C:10]1[C:11]([F:21])=[CH:12][C:13]([NH2:18])=[C:14]([O:16][CH3:17])[CH:15]=1

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 223473121-Bromo-2-fluoro-5-methoxy-4-nitrobenzene

Product 1

HCID 223472984-Bromo-5-fluoro-2-methoxyanilineYield 40.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium hydrosulfite (14.7 g, 84.4 mmol) was added to a solution of 1-bromo-2-fluoro-5-methoxy-4-nitrobenzene (9.28 g, 37.12 mmol) in ethanol (180 mL) and water (130 mL) at 80° C. in three portions. After 5 hours the organic solvent was removed and the solid in aqueous layer was collected by filtration. The solid was further washed with heptane/ethyl acetate (3:2, 400 mL). The filtrate was evaporated to give 4-bromo-5-fluoro-2-methoxyaniline (3.29 g, 40%). 1H NMR (DMSO-d6) δ 3.75 (s, 3H), 5.22 (s, 2H), 6.56 (d, J=10.68 Hz, 2H), 6.94 (d, J=6.57 Hz, 2H).

Workup

  1. customAfter 5 hours the organic solvent was removed
  2. filtrationthe solid in aqueous layer was collected by filtration
  3. washThe solid was further washed with heptane/ethyl acetate (3:2, 400 mL)
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-69af3ef457534916a4b5def4d8bd131e
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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