2-Aminophenol → 3-bromo-N-(2-hydroxyphenyl)4-methylbenzamide

HRID 7687

Reaction equation

HRID 7687 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=O.S(Cl)(Cl)=O.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23].C(N(C(C)C)CC)(C)C>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23])=[O:7]

Participants

6

Reactant 4

HCID 58012-AminophenolHCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 821303-Bromo-4-methylbenzoic acid

Product 1

HCID 219909653-bromo-N-(2-hydroxyphenyl)4-methylbenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-bromo-4-methylbenzoic acid (1.0 g, 4.7 mmol) and thionyl chloride (18 mL) was refluxed for 1 h and then cooled to rt. The excess thionyl chloride was removed int vacuo, the residue was dissolved in THF (10 mL), and it was added to a cooled (0° C.) mixture of 2-aminophenol (507 mg, 4.7 mmol) and diisopropylethylamine (0.90 mL; 5.1 mmol) in THF (18 mL). The resulting mixture was stirred at rt for 4 h. The solvent was then removed and the residue was purified by flash chromatography on silica gel eluting with EtOAc:hexanes (1:5 to 1:4) to afford 3-bromo-N-(2-hydroxyphenyl)-4-methylbenzamide.

Workup

  1. temperaturewas refluxed for 1 h
  2. customThe excess thionyl chloride was removed int vacuo
  3. dissolutionthe residue was dissolved in THF (10 mL)
  4. additionit was added to
  5. temperaturea cooled
  6. customThe solvent was then removed
  7. customthe residue was purified by flash chromatography on silica gel eluting with EtOAc:hexanes (1:5 to 1:4)

Sources & evidence

ORD record
ord-8c9853080e9e4c4981f9fefb9aec9e45
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Linked notes

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