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

HRID 1598352Notes

Reaction equation

HRID 1598352 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) δ3.08 (s, 3 H), 3.79 (s, 2 H), 5.35 (s, 2 H), 7.06 (s, t, J=9 Hz, 2 H), 7.32 (dd, J=6 and 9 Hz, 2 H), 8.06 (s, 4 H).

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-42892034e9724649a228993633c5eef0
Source dataset
uspto-grants-1998_04
Patent number
US05736579

Reaction notes

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