Triethylamine → 2-Allyloxy-4-fluoro-phenylamine

HRID 450037Notes

Reaction equation

HRID 450037 reaction equation
O.[Sn](Cl)Cl.[CH2:5]([O:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[N+:16]([O-])=O)[CH:6]=[CH2:7].C(N(CC)CC)C>C(OCC)(=O)C>[CH2:5]([O:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[NH2:16])[CH:6]=[CH2:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 197026902-(Allyloxy)-4-fluoro-1-nitrobenzeneHCID 43835034Tin dichloride dihydrate

Product 1

HCID 624927772-Allyloxy-4-fluoro-phenylamineYield 50%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Tin (II) chloride hydrate (8.5 g, 38 mmol, 5 eq) was added to a solution of 2-allyloxy-4-fluoro-1-nitro-benzene (1.5 g, 7.6 mmol) in ethyl acetate (20 ml) at room temperature and the mixture was stirred for 4 hr. The reaction mixture was neutralized with triethylamine and then partitioned between water and ethyl acetate. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated to dryness to give 2-allyloxy-4-fluoro-phenylamine (0.6 g, 50%). The crude compound was used in the next stage without purification.

Workup

  1. custompartitioned between water and ethyl acetate
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-a9b68709ee2b4a5e981bc621a46a9ebf
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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