Trimethyl orthoformate → HCID 58487139, compound

HRID 874611Notes

Reaction equation

HRID 874611 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].F[C:13](F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.C(OC)(OC)OC>CCO.CC(=O)OCC.CCCCCC>[Br:9][C:5]1[C:6]([CH3:8])=[CH:7][C:2]2[N:1]=[CH:13][O:10][C:3]=2[CH:4]=1

Participants

7

Reactant 3

HCID 9005Trimethyl orthoformateHCID 2733225Ytterbium triflateHCID 58486931HCID 58486931, compound

Product 1

HCID 58487139HCID 58487139, compoundYield 1,344.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
90 °C

Procedure

A mixture of 2-amino-5-bromo-4-methylphenol (42) (290 mg), trifluoromethanesulfonic acid Ytterbium (III) salt (20 mg) and trimethyl orthoformate (185 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 91.9 mg 6-bromo-5-methylbenzoxazole (43) as yellow solid (yield: 38%)

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-01d7da7596ad4cb6a7a1dd44d5c605c6
Source dataset
uspto-grants-2015_03
Patent number
US08980629B2

Reaction notes

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