Trimethyl orthoacetate → 6-Bromo-5-chloro-2-methylbenzoxazole

HRID 874607Notes

Reaction equation

HRID 874607 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Br:9])=[CH:4][C:3]=1[OH:10].[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.[C:36](OC)(OC)(OC)[CH3:37]>CCO>[Br:9][C:5]1[C:6]([Cl:8])=[CH:7][C:2]2[N:1]=[C:36]([CH3:37])[O:10][C:3]=2[CH:4]=1

Participants

5

Reactant 3

HCID 15050Trimethyl orthoacetateHCID 2733225Ytterbium triflateHCID 584871002-Amino-5-bromo-4-chlorophenol

Product 1

HCID 584874386-Bromo-5-chloro-2-methylbenzoxazoleYield 80.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-amino-5-bromo-4-chlorophenol (29) (865 mg, 3.89 mmol), trifluoromethanesulfonic acid Ytterbium (III) salt (24 mg, 1% mol) and trimethyl orthoacetate (610 μl, 1.2 eq.) in 3 ml EtOH was heated at 90° C. for 1 h. After cooling down to r.t., off-white needles fell off, which were filtered, washed with MeOH, water and dried to give 791 mg title compound as off-white crystalline solid. Yield: 80.2%; purity>95%.

Workup

  1. temperatureAfter cooling down to r.t.
  2. filtrationwhich were filtered
  3. washwashed with MeOH, water
  4. customdried

Sources & evidence

ORD record
ord-6edd2783945043359322722f5372ee39
Source dataset
uspto-grants-2015_03
Patent number
US08980629B2

Reaction notes

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