Benzoyl chloride → 3-Benzoyloxy-4-fluorotoluene

HRID 19935Notes

Reaction equation

HRID 19935 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=1[OH:18].C(N(CC)CC)C>ClCCl>[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=1[O:18][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 182387Phenol, 2-fluoro-5-methyl-

Product 1

HCID 167492203-Benzoyloxy-4-fluorotoluene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzoyl chloride (4.22 g, 30 mmol) was added dropwise with a syringe to a solution of 2-fluoro-5-methylphenol (3.784 g, 30 mmol) and triethylamine (5 mL) in dichloromethane (50 mL), The mixture was stirred for 18 h at room temperature and concentrated under reduced pressure. Diethyl ether (200 mL) and water (100 mL) were added, the organic layer was separated and extracted with 2N NaOH (2×30 mL) and brine (20 mL), dried over sodium sulphate and concentrated under reduced pressure to give a white solid. Yield: 6.601 g (96%). 1H-NMR (400 MHz, CDCl3) δ=2.36 (s, 3H, —CH3), 7.01-7.12 (m, 3H), 7.49-7.55 (m, 2H), 7.63-7.68 (m, 1H), 8.19-8.23 (m, 2H). LRMS (FAB+): 231.1 (100, [M+H]+).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionDiethyl ether (200 mL) and water (100 mL) were added
  3. customthe organic layer was separated
  4. extractionextracted with 2N NaOH (2×30 mL) and brine (20 mL)
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customto give a white solid

Sources & evidence

ORD record
ord-5991427e33334824bfef067394e4f07a
Source dataset
uspto-grants-2010_06
Patent number
US07745472B2

Reaction notes

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