Trimethyl orthoacetate → HCID 58486775, compound

HRID 874614Notes

Reaction equation

HRID 874614 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[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.CC(=O)OCC>[Br:9][C:5]1[C:6]([CH3:8])=[CH:7][C:2]2[N:1]=[C:36]([CH3:37])[O:10][C:3]=2[CH:4]=1

Participants

6

Reactant 3

HCID 15050Trimethyl orthoacetateHCID 2733225Ytterbium triflateHCID 58486931HCID 58486931, compound

Product 1

HCID 58486775HCID 58486775, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-amino-5-bromo-4-methylphenol (42) (290 mg), trifluoromethanesulfonic acid Ytterbium (III) salt (20 mg, 1% mol) and trimethyl orthoacetate (216 μl, 1.5 eq.) in 2 ml EtOH was heated at 90° C. for 2 h. After cooling down to r.t., the reaction mixture was taken up in EA, washed with aq. NaHCO3 and brine, dried over Na2SO4, concentrated to dryness. The resulting brown solid was dissolved in DCM and subjected to silica gel column purification using 0-60% B (A: hexane; B: 50% EA in hexane) to furnish 148 mg 6-bromo-2,5-dimethylbenzoxazole (48) as pale brown solid.

Workup

  1. temperatureAfter cooling down to r.t.
  2. washwashed with aq. NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness
  5. dissolutionThe resulting brown solid was dissolved in DCM
  6. customsubjected to silica gel column purification

Sources & evidence

ORD record
ord-6042b2409ae54e11a5c76d57baa2ef53
Source dataset
uspto-grants-2015_03
Patent number
US08980629B2

Reaction notes

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