Cyanogen Bromide → HCID 67311166, compound

HRID 2190484Notes

Reaction equation

HRID 2190484 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=2)[C:10]([O:12][CH3:13])=[O:11])=[CH:4][C:3]=1[OH:19].[N:20]#[C:21]Br>O1CCCC1.C(OCC)(=O)C>[NH2:20][C:21]1[O:19][C:3]2[CH:4]=[C:5]([O:6][C:7]3[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=3)[C:10]([O:12][CH3:13])=[O:11])[CH:17]=[CH:18][C:2]=2[N:1]=1

Participants

5

Reactant 2

HCID 10476Cyanogen Bromide2×HCID 67313230HCID 67313230, compound

Product 1

HCID 67311166HCID 67311166, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 3-(4-amino-3-hydroxyphenoxy)benzoate (13.1 g, 50.5 mmol) in tetrahydrofuran (200 mL) was added cyanogen bromide (9.76 g, 92.1 mmol), and the mixture was stirred at room temperature for 16 hr. To the reaction mixture was added cyanogen bromide (1.78 g, 16.8 g), and the mixture was further stirred at room temperature for 3 days. The reaction mixture was diluted with ethyl acetate (300 mL), washed with saturated aqueous sodium hydrogencarbonate solution (150 mL×2) and saturated brine (150 mL), successively, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (13.6 g, yield (total of 4 steps) 95%) as brown crystals.

Workup

  1. stirringthe mixture was further stirred at room temperature for 3 days
  2. washwashed with saturated aqueous sodium hydrogencarbonate solution (150 mL×2) and saturated brine (150 mL)
  3. dry with materialsuccessively, and dried over anhydrous magnesium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-62f910699d144475ad3152474fd10026
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

Loading…