Sodium Hydroxide → HCID 12040848, compound

HRID 1681091Notes

Reaction equation

HRID 1681091 reaction equation
[NH2:1][C:2]1[C:3]([CH2:11][C:12](Cl)=[CH2:13])=[C:4]([OH:10])[C:5]([Cl:9])=[CH:6][C:7]=1[F:8].FC(F)(F)S(O)(=O)=O.[OH-].[Na+]>C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:3]2[CH:11]=[C:12]([CH3:13])[O:10][C:4]=2[C:5]([Cl:9])=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 19806965HCID 19806965, compound

Product 1

HCID 12040848HCID 12040848, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Amino-6-chloro-2-(2-chloro-2-propenyl)-4-fluorophenol (4.8 g) was dissolved in chloroform (20 ml), and trifluoromethanesulfonic acid (4.6 g)was dropwise added thereto at 5° C. for 5 minutes, followed by stirring at room temperature for 5 hours. After completion of the reaction, the reaction mixture was poured into a 5% NaOH solution (30 ml) at 5° C. and extracted with ethyl acetate. The organic layer was dried and concentrated to give 4-amino-7-chloro-5-fluoro-2-methylbenzo[b]furan (3.5 g; yield, 86%).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3f1965a07a5b467faa89061823878070
Source dataset
uspto-grants-1992_12
Patent number
US05169431

Reaction notes

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