Benzoyl chloride → 3-Benzoyloxy-4-fluorotoluene

HRID 1685646Notes

Reaction equation

HRID 1685646 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[OH:9].CCN(CC)CC.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)Cl>[C:17]([O:9][C:3]1[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=1[F:1])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

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

Product 1

HCID 167492203-Benzoyloxy-4-fluorotolueneYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-fluoro-3-hydroxytoluene (3.784 g, 30 mmol)) in CH2Cl2 (50 mL) was added NEt3 (5 mL) and the mixture stirred at room temperature for 0.5 h. Benzoyl chloride (4.22 mL, 30 mmol) was then added and the reaction stirred at room temperature for 18 h. The reaction was concentrated in vacuo and the residue redissolved in Et2O (200 mL), washed with water (100 mL), 2N NaOH (2×30 mL) and brine (20 mL). The ethereal layer was dried (Na2SO4) and concentrated in vacuo to give 3-benzoyloxy-4-fluorotoluene as a white solid (6.601 g, 96%), which was used without futher purification. δH (400 MHz, CDCl3) 2.36 (s, 3H), 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+) m/z (rel. intensity) 231.1 (100, [M+H]+)

Workup

  1. stirringthe reaction stirred at room temperature for 18 h
  2. concentrationThe reaction was concentrated in vacuo
  3. dissolutionthe residue redissolved in Et2O (200 mL)
  4. washwashed with water (100 mL), 2N NaOH (2×30 mL) and brine (20 mL)
  5. dry with materialThe ethereal layer was dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-255e07f5f8024d08a9ba32fba8ebf715
Source dataset
uspto-grants-2012_04
Patent number
US08148415B2

Reaction notes

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