Benzyl Bromide → HCID 68763871, compound

HRID 1169880Notes

Reaction equation

HRID 1169880 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](O)=[C:6]([CH:10]=1)[C:7]([NH2:9])=[O:8].[C:12]([O-:15])([O-])=O.[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:18]([O:15][CH3:12])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:6]([CH:10]=1)[C:7]([NH2:9])=[O:8]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 3480945-Chloro-2-hydroxybenzamide

Product 1

HCID 68763871HCID 68763871, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Chloro-2-hydroxy-benzamide (1.5 g, 8.7 mmol) was dissolved in DMF (120 mL) and to the stirred solution K2CO3 (1.38 g, 10 mmol) and benzylbromide (1.71 g, 10 mmol) were added. The mixture was stirred at room temperature overnight. The suspension was concentrated in vacuo, and the residue was partitioned between water (30 mL) and Et2O (30 mL). The aqueous phase was separated and extracted with ether (20 mL×2). The combined organic phases were dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate 90/10), to give 75 as a white solid (2.15 g, 95%). 1H NMR (CDCl3, 300 MHz) δ8.20 (d, J=3 Hz, 1H), 7.67 (br s, 1H), δ7.44-7.38(m, 6H), 7.99 (d, J=9 Hz, 1H), 5.85 (br s, 1H), 5.17 (s, 2H). MS (m/e) (positive FAB) 262.1 (M+H)+. m.p. 110-112° C.

Workup

  1. additionwere added
  2. concentrationThe suspension was concentrated in vacuo
  3. customthe residue was partitioned between water (30 mL) and Et2O (30 mL)
  4. customThe aqueous phase was separated
  5. extractionextracted with ether (20 mL×2)
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate 90/10)

Sources & evidence

ORD record
ord-b76e129645ea4acfa9aba7668f3a4a83
Source dataset
uspto-grants-2010_11
Patent number
US07825126B2

Reaction notes

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