Diisopropylethylamine → HCID 57424208, compound

HRID 2377309Notes

Reaction equation

HRID 2377309 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([OH:12])=[O:11].C(N(CC)C(C)C)(C)C.[C:22]([O:25][CH2:26]Br)(=[O:24])[CH3:23].CCC(OBr)=O>C(#N)C>[C:22]([O:25][CH2:26][O:11][C:10](=[O:12])[CH2:9][C:3]1[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=1[F:1])(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 222403932-(2-Fluoro-4-iodophenyl)acetic acidHCID 86600378HCID 86600378, compound

Product 1

HCID 57424208HCID 57424208, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-fluoro-4-iodo phenyl acetic acid (described in U.S. Pat. No. 6,252,090, incorporated herein by reference;, 0.82 g, 2.93 mmol) in anhydrous acetonitrile (10 mL) was treated with N,N-diisopropyl ethyl amine (1.27 mL, 7.32 mmol) followed by acetoxy methyl bromide/bromo methylacetate (0.896 g, 5.86 mmol) and the resulting reaction mixture was stirred overnight at ambient temperature. The volatiles were evaporated in vacuo and the residue was diluted with water and extracted with diethyl ether (×2). The combined organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to an oil that was subjected to flash column chromatography over silica gel (230-400 mesh) using 10-20% ethyl acetate in hexane as the eluent to afford the title compound as an oil (0.75 g, 72%). 1H NMR (300 MHz, CDCl3): 7.42(m, 2H), 6.97(dd, J=8.0 & 8.0 Hz, 1H), 5.73(s, 2H), 3.65(s, 2H), 2.08 (s, 3H).

Workup

  1. customthe resulting reaction mixture
  2. customThe volatiles were evaporated in vacuo
  3. additionthe residue was diluted with water
  4. extractionextracted with diethyl ether (×2)
  5. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo to an oil that

Sources & evidence

ORD record
ord-5cab4af887a341b6a5aba58cb1113e55
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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