Methanol → HCID 21310735, compound

HRID 583183Notes

Reaction equation

HRID 583183 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([O:11]C)[C:3]=1[NH:13][C:14](=[O:16])[CH3:15].B(Br)(Br)Br.CO.CCCCCC.CCOC(C)=O>C(Cl)Cl.C(Cl)Cl.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([OH:11])[C:3]=1[NH:13][C:14](=[O:16])[CH3:15]

Participants

7

Reactant 4

HCID 887MethanolHCID 25134Boron tribromideHCID 21226206Ethyl acetate hexaneHCID 21310736HCID 21310736, compound

Product 1

HCID 21310735HCID 21310735, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

To a slurry of 1.26 g of N-(2-bromo-6-methoxy-4-nitrophenyl)acetamide and 60 mL of methylene chloride at 0° C., 8.7 mL of 1.0 M BBr3 in methylene chloride was added dropwise. The mixture was slowly warmed to rt. and allowed to react overnight. MeOH was added next morning and allowed to stir for 10 min. TLC(50/50 hexane/EtOAc) showed reaction complete, different conditions(90/10 DCM/EtOAc) showed there to be two products. Added satd. NaHCO3, extracted with EtOAc(2×), dried organic over MgSO4 and conc. in vacuo. Recovered 1.16 g of product, NMR(CDCl3 400 MHz) showed the two products to be desired and 4-bromo-2-methyl-6-nitro-benzooxazole. The product was carried on with no fiuther purification.

Workup

  1. customto react overnight
  2. customreaction complete
  3. additionAdded
  4. extractionNaHCO3, extracted with EtOAc(2×), dried organic over MgSO4 and conc. in vacuo
  5. customRecovered 1.16 g of product, NMR(CDCl3 400 MHz)
  6. customThe product was carried on with no fiuther purification

Sources & evidence

ORD record
ord-d76d5b35591d4af3b5f4f89a4c489685
Source dataset
uspto-grants-1999_07
Patent number
US05929094

Reaction notes

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