Acetyl bromide → HCID 21886672, compound

HRID 2216059Notes

Reaction equation

HRID 2216059 reaction equation
C([Br:4])(=O)C.[N+]([C:8]1[CH:13]=[CH:12][N:11]([OH:14])[CH2:10][C:9]=1[CH3:15])([O-])=O>>[Br:4][C:8]1[CH:13]=[CH:12][N:11]([OH:14])[CH2:10][C:9]=1[CH3:15]

Participants

3

Reactant 2

HCID 10482Acetyl bromideHCID 21886633HCID 21886633, compound

Product 1

HCID 21886672HCID 21886672, compoundYield 86%

Conditions

Temperature
50 °C

Procedure

Acetyl bromide (5 mL) was cooled to 0° C. To this was added 4-Nitro-3-methyl-pyridin-1-ol (1000 mg, 6.48 mmol) portionwise while maintaining temperature. After the addition was complete, the reaction was heated to 50° C. and stirred for 2 hours. The reaction was then cooled to 0° C., quenched with ice and neutralized with solid Na2CO3 (pH=8). The neutral aqueous reaction mixture was extracted into DCM. The organic layer was dried (MgSO4), the solvents were removed in vacuo resulting in the title compound as a yellow solid (1.05 mg, 86%). ESI-MS (m/z): Calcd. for C6H6BrNO: 188.0 (M+1); found: 188.0.

Workup

  1. temperaturewhile maintaining temperature
  2. additionAfter the addition
  3. temperatureThe reaction was then cooled to 0° C.
  4. customquenched with ice and neutralized with solid Na2CO3 (pH=8)
  5. extractionThe neutral aqueous reaction mixture was extracted into DCM
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-5f05e7fb670c456ca0a6e228f414d39d
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

Loading…