Dimethylformamide → HCID 61395608, compound

HRID 2358740Notes

Reaction equation

HRID 2358740 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[C:12]([O-:15])([O-])=[O:13].[K+].[K+].CN([CH:21]=[O:22])C>>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([O:22][C:21]2[CH:4]=[C:3]([CH:2]=[CH:7][CH:6]=2)[C:12]([OH:15])=[O:13])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27949042-Bromo-5-chloronitrobenzene

Product 1

HCID 61395608HCID 61395608, compound

Conditions

Temperature
85 °C

Procedure

To a solution of DMF (50 mL) was added 1-bromo-2-nitro-4-chloro-benzene (10.0 g, 42.2 mmol), 3-hydxoxybenzoic acid (5.8 g, 42.0 mmol), and K2CO3 (17.5 g, 0.13 mol). The solution was heated to 85° C. and stirred overnight. The reaction was poured into distill water and extracted with ethyl acetate. The combined organic layers were washed with distilled water, brine, and dried over Na2SO4, filtered and concentrated under vacuum giving a crude oil. This oil was purified by silica gel column chromatography eluting with CH2Cl2/MeOH (90:10) to give the title compound (7.4 gm, 60

Workup

  1. additionThe reaction was poured
  2. distillationinto distill water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with distilled water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customgiving a crude oil
  9. customThis oil was purified by silica gel column chromatography
  10. washeluting with CH2Cl2/MeOH (90:10)

Sources & evidence

ORD record
ord-68d203570612481e8adeb26ad43a84f1
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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