Water → HCID 86638986, compound

HRID 889269Notes

Reaction equation

HRID 889269 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([O:16][C:17]1[C:22]([NH2:23])=[C:21]([F:24])[C:20]([F:25])=[CH:19][CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O>ClCCl>[CH2:9]([O:16][C:17]1[C:22]([NH2:23])=[C:21]([F:24])[C:20]([F:25])=[C:19]([Br:1])[CH:18]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 68431616HCID 68431616, compound

Product 1

HCID 86638986HCID 86638986, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A round bottom flask containing N-bromosuccinimide (0.52 mg, 2.93 mmol), and dichloromethane (5 mL) is stirred in an ice bath. A solution of the 6-benzyloxy-2,3-difluoro-phenylamine (0.69 mg, 2.93 mmol) in 10 mL of dichloromethane is added quickly in one portion. The resulting mixture is stirred for 20 min then water is added and the resulting mixture is extracted twice with DCM. The organic portion is dried over MgSO4, filtered and concentrated to afford the title compound, which is used directly in the next step without purification.

Workup

  1. stirringThe resulting mixture is stirred for 20 min
  2. extractionthe resulting mixture is extracted twice with DCM
  3. dry with materialThe organic portion is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fa0218f3b7894683b540a69f9d1ca511
Source dataset
uspto-grants-2012_08
Patent number
US08252820B2

Reaction notes

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