Triethylamine → 2-(4-(Methylsulfonyl)phenyl)-2-oxoethyl 2-(4-fluorophenyl)acetate

HRID 275478

Reaction equation

HRID 275478 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.Br[CH2:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1)=[O:22]>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:20][C:21]([C:23]2[CH:24]=[CH:25][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:27][CH:28]=2)=[O:22])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 98372-(4-Fluorophenyl)acetic acidHCID 7358232-Bromo-4'-(methylsulfonyl)acetophenone

Product 1

HCID 189338812-(4-(Methylsulfonyl)phenyl)-2-oxoethyl 2-(4-fluorophenyl)acetateYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 4.45 g (28.9 mmol) of 4-fluorophenylacetic acid in 3.26 g (31.8 mmol) of triethylamine and 275 mL of acetonitrile was added 8.9 g (28.9 mmol) of 2-bromo-4'-(methylsulfonyl)acetophenone (prepared in Step 3) at ambient temperature. The reaction mixture was stirred for 30 minutes, concentrated in vacuo, and partitioned between ethyl acetate and water. The organic phase was dried (MgSO4) and concentrated in vacuo. Purification by silica gel chromatography with ethyl acetate/hexane (1:1) gave 6.87 g (68%) of 2-(4-fluorophenyl)-1-[2-[4-(methylsulfonyl) phenyl]-2-oxoethoxy]ethanone as a colorless solid: NMR (CDCl3) δ 3.08 (s, 3H), 3.79 (s, 2H), 5.35 (s, 2H), 7.06 (s, t, J=9 Hz, 2H), 7.32 (dd, J=6and 9 Hz, 2H), 8.06 (s, 4H).

Workup

  1. concentrationconcentrated in vacuo
  2. custompartitioned between ethyl acetate and water
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by silica gel chromatography with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-3377be980e814afb9b03c36ff6557afe
Source dataset
uspto-grants-1995_02
Patent number
US05393790

Linked notes

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