Phenol → HCID 522791, compound

HRID 2377252Notes

Reaction equation

HRID 2377252 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[Br:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19](Cl)=[O:20]>C(OCC)C>[Br:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19]([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:20]

Participants

5

Reactant 3

HCID 996PhenolHCID 8471TriethylamineHCID 74377Benzoyl chloride, 3-bromo-

Product 1

HCID 522791HCID 522791, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of phenol (2.3 g, 24.4 mmol) and triethylamine (3.2 g, 32 mmol) in diethyl ether (150 mL) was slowly added 3-bromobenzoyl chloride (5 g, 22.8 mmol) and the mixture was heated to reflux for about 1 hour. The mixture was cooled, filtered, and the filtrate was successively washed with water, 0.2N hydrochloric acid, and saturated aqueous sodium carbonate. The organic layer was dried (MgSO4), filtered, and concentrated under vacuum. The residue was triturated with hexane and dried under vacuum to provide the desired product. 1H NMR (500 MHz, CDCl3) δ 7.22 (m, 3H), 7.42 (m, 3H), 7.79 (d, J=8 Hz, 1H), 8.15 (d, J=8 Hz, 1H), 8.37 (br s, 1H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for about 1 hour
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. washthe filtrate was successively washed with water, 0.2N hydrochloric acid, and saturated aqueous sodium carbonate
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe residue was triturated with hexane
  10. customdried under vacuum

Sources & evidence

ORD record
ord-9a01196cb00b4bf9944c4181f39927d8
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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