Hydrochloric Acid → HCID 23130240, compound

HRID 2114163Notes

Reaction equation

HRID 2114163 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([F:15])=[CH:13][C:12]([NH2:16])=[CH:11][C:10]=1[F:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O.Cl>C1COCC1>[CH2:1]([O:8][C:9]1[C:10]([F:17])=[CH:11][C:12]([NH2:16])=[C:13]([Br:18])[C:14]=1[F:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 67184N-bromobutanimideHCID 23130273HCID 23130273, compound

Product 1

HCID 23130240HCID 23130240, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-benzyloxy-3,5-difluorophenylamine (3.0 g) in THF (30 mL) was added N-bromosuccinimide (2.32 g) under ice-cooling, and the mixture was stirred for 30 minutes. Conc. Hydrochloric acid (2 mL) was added to the reaction mixture to precipitate a solid. The solid was collected by filtration and dried. The dried solid was dissolved in water, and the solution was added with saturated aqueous sodium bicarbonate, and then extracted with ethyl acetate. The extract was dried over sodium sulfate and concentrated to give 4-benzyloxy-2-bromo-3,5-difluorophenylamine (3.33 g).

Workup

  1. temperaturecooling
  2. customto precipitate a solid
  3. filtrationThe solid was collected by filtration
  4. customdried
  5. dissolutionThe dried solid was dissolved in water
  6. additionthe solution was added with saturated aqueous sodium bicarbonate
  7. extractionextracted with ethyl acetate
  8. dry with materialThe extract was dried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-c5973936a2b4490ea56d8f023888919b
Source dataset
uspto-grants-2008_10
Patent number
US07432392B2

Reaction notes

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