Stannous chloride dihydrate → 2-Fluoro-6-(2-propyn-1-yloxy)benzenamine

HRID 1688092Notes

Reaction equation

HRID 1688092 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][C:10]#[CH:11])[C:3]=1[N+:12]([O-])=O.O.O.[Sn](Cl)Cl>CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][C:10]#[CH:11])[C:3]=1[NH2:12]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 62665059HCID 62665059, compound

Product 1

HCID 866340822-Fluoro-6-(2-propyn-1-yloxy)benzenamineYield 38.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 1-fluoro-2-nitro-3-prop-2-ynyloxy-benzene (460 mg) in EtOAc (50 mL), was added tin(II) chloride dihydrate with stirring. After 6 hours the mixture was diluted with EtOAc and washed 3 times with brine. The organic layer was dried with sodium sulfate, concentrated and the residue purified by silica gel chromatography to afford 150 mg of 2-fluoro-6-prop-2-ynyloxy-phenylamine: 1H NMR (300 MHz, CDCl3) δ 6.9-6.7 (m, 3H), 4.8 (s, 2H), 4.0 (bs, 2H), 2.6 (s, 1H).

Workup

  1. washwashed 3 times with brine
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. concentrationconcentrated
  4. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-315f4080b4d442098cebccefd20cd7ca
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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