Hydrochloric Acid → HCID 58303855, compound

HRID 1404124Notes

Reaction equation

HRID 1404124 reaction equation
[Br:1][C:2]1[C:3]([N+:13]([O-])=O)=[C:4]([Cl:12])[CH:5]=[C:6]([F:11])[C:7]=1[O:8][CH2:9][CH3:10].Cl.Cl[Sn]Cl.O>C(O)C>[Br:1][C:2]1[C:7]([O:8][CH2:9][CH3:10])=[C:6]([F:11])[CH:5]=[C:4]([Cl:12])[C:3]=1[NH2:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 24479Stannous ChlorideHCID 58304006Benzene, 3-bromo-1-chloro-4-ethoxy-5-fluoro-2-nitro-

Product 1

HCID 58303855HCID 58303855, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 30-4 (22.9 g, 77 mmol) in ethanol (100 mL) at room temperature was added concentrated HCl (74 mL) and SnCl2 (44 g, 231 mmol). The mixture was allowed to stir at room temperature for 4 hours. The reaction mixture was poured into water and extracted with ethyl acetate (3×150 mL), the organic layer was combined and was concentrated under vacuum to get a crude product which was purified on silica gel column chromatography eluting with petroleum ether/ethyl acetate (5:1 to 1:1) to afford 30-5 (16 g, 78%) as a white solid. LRMS: calc 266.9 and found: 267.9 [M+1].

Workup

  1. extractionextracted with ethyl acetate (3×150 mL)
  2. concentrationwas concentrated under vacuum
  3. customto get a crude product which
  4. customwas purified on silica gel column chromatography
  5. washeluting with petroleum ether/ethyl acetate (5:1 to 1:1)

Sources & evidence

ORD record
ord-097b46779c0a43fe8c5fb42553bc9faa
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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