Benzoic Acid → 6-Bromo-2-phenylbenzo[d]oxazole

HRID 1619915Notes

Reaction equation

HRID 1619915 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([OH:9])[CH:3]=1.[C:10](O)(=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.B(O)(O)O.O>C1(C)C(C)=CC=CC=1.C(Cl)Cl>[Br:1][C:2]1[CH:8]=[CH:7][C:5]2[N:6]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:9][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 243Benzoic AcidHCID 962WaterHCID 7628Boric AcidHCID 143206052-Amino-5-bromophenol

Product 1

HCID 230259476-Bromo-2-phenylbenzo[d]oxazole

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7237O-XyleneSolvent

Procedure

38.65 g (205.56 mmol) 4-bromo-2-hydroxy-aniline are boiled together with 25.10 g (205.56 mmol) benzoic acid and 12.75 g (205.56 mmol) boric acid in 500 ml of xylene for 6 days using the water separator. The solv. is eliminated in vacuo and the residue is taken up in DCM. The mixture is extracted 1× each with 1N sodium hydroxide solution, water, 2N hydrochloric acid and again with water. The org. phase is concentrated i. V. by rotary evaporation and the residue is separated through silica gel (eluant cyclohexane/EA).

Workup

  1. extractionThe mixture is extracted 1× each with 1N sodium hydroxide solution, water, 2N hydrochloric acid
  2. concentrationphase is concentrated i
  3. customby rotary evaporation
  4. customthe residue is separated through silica gel (eluant cyclohexane/EA)

Sources & evidence

ORD record
ord-d53248a87145481687218c208b0dcbaa
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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