Sulfuric Acid → 5-Bromo-2-cyclopropylphenol

HRID 1945282Notes

Reaction equation

HRID 1945282 reaction equation
OS(O)(=O)=O.[Br:6][C:7]1[CH:8]=[CH:9][C:10]([CH:14]2[CH2:16][CH2:15]2)=[C:11]([CH:13]=1)N.N([O-])=[O:18].[Na+]>O>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([CH:14]2[CH2:16][CH2:15]2)=[C:11]([OH:18])[CH:13]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 47122485-Bromo-2-cyclopropylanilineHCID 23668193Sodium Nitrite

Product 1

HCID 135793835-Bromo-2-cyclopropylphenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

An ice-cold solution of H2SO4 (0.23 mL, 4.31 mmol) in water (2 mL) was added to 5-bromo-2-cyclopropylaniline (300 mg, 1.42 mmol) at 0° C. The reaction was stirred for 10 min, then sodium nitrite (98 mg, 1.415 mmol) in 2 mL cold water was added dropwise. The reaction was stirred at 0° C. for 1 h and then heated at 100° C. for 1 h. Reaction was extracted with EtOAc. Combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated to afford the title compound, which was used without further purification. LC-MS calculated for C9H9BrO 211.98, no ionization, (Rt: 1.57/4 min.).

Workup

  1. stirringThe reaction was stirred at 0° C. for 1 h
  2. customReaction
  3. extractionwas extracted with EtOAc
  4. washCombined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0a2c3fad5851451387a248af2ff39271
Source dataset
uspto-grants-2013_03
Patent number
US08394969B2

Reaction notes

Loading…