Water → 1-Bromo-3-fluoro-5-nitrobenzene

HRID 1452053Notes

Reaction equation

HRID 1452053 reaction equation
O.S(=O)(=O)(O)O.[F:7][C:8]1[CH:14]=[C:13]([Br:15])[C:11](N)=[C:10]([N+:16]([O-:18])=[O:17])[CH:9]=1.N([O-])=O.[Na+]>C(O)C>[Br:15][C:13]1[CH:11]=[C:10]([N+:16]([O-:18])=[O:17])[CH:9]=[C:8]([F:7])[CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 2920042-Bromo-4-fluoro-6-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 150201571-Bromo-3-fluoro-5-nitrobenzeneYield 49.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Mix water (60mL), concentrated sulfuric acid (60mL) and 4-fluoro-2-nitro-6-bromoaniline (9.65g, 41mmol). Cool to 0° C. and add solid sodium nitrite (4.25g, 61mmol) in small portions at such a rate as not to exceed 5° C. Stir for 30 minutes and add ferrous sulfate heptahydrate (5.6g, 20.5mmol) and ethanol (18mL). Stir with warming to room temperature over 2 hours. Add water (200mL), separate the organic phase and wash the aqueous phase with methylene chloride (2×). Combine the organic phases, dry (MgSO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography (5% ethyl acetate/hexane) give 3-bromo-5-fluoronitrobenzene (4.5g); bp 65°-70° [email protected] Hg.

Workup

  1. customto exceed 5° C
  2. stirringStir
  3. temperaturewith warming to room temperature over 2 hours
  4. customAdd water (200mL), separate the organic phase
  5. washwash the aqueous phase with methylene chloride (2×)
  6. dry with materialCombine the organic phases, dry (MgSO4)
  7. customevaporate the solvent in vacuo
  8. customPurify by silica gel chromatography (5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c82781fbe2f74c65b8c2763442d20901
Source dataset
uspto-grants-1997_02
Patent number
US05606063

Reaction notes

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