Iodine → 2-(2-Heptafluoropropylbenzoxazol-5-yl)propionic acid

HRID 48165Notes

Reaction equation

HRID 48165 reaction equation
[F:1][C:2]([F:25])([C:21]([F:24])([F:23])[F:22])[C:3]([F:20])([F:19])[C:4]1[O:5][C:6]2[CH:12]=[CH:11][C:10]([CH:13]([CH3:18])[C:14]([O:16]C)=[O:15])=[CH:9][C:7]=2[N:8]=1.C[Si](C)(C)[Si](C)(C)C.II.C1(C)C=CC=CC=1>C(OCC)(=O)C>[F:25][C:2]([F:1])([C:21]([F:22])([F:23])[F:24])[C:3]([F:19])([F:20])[C:4]1[O:5][C:6]2[CH:12]=[CH:11][C:10]([CH:13]([CH3:18])[C:14]([OH:16])=[O:15])=[CH:9][C:7]=2[N:8]=1

Participants

6

Reactant 4

HCID 807IodineHCID 1140TolueneHCID 74057HexamethyldisilaneHCID 22742104Methyl 2-(2-heptafluoropropylbenzoxazol-5-yl)propionate

Product 1

HCID 227420902-(2-Heptafluoropropylbenzoxazol-5-yl)propionic acidYield 56.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 2-(2-heptafluoropropylbenzoxazol-5-yl)propionate (11.6 g, 0.0311 mol), hexamethyldisilane (6.81 g, 0.047 mol) and iodine (11.85 g, 0.047 mol) was stirred in refluxing toluene (110 ml) for 6 hours. The mixture was cooled to room temperature, diluted with ethyl acetate and washed sequentially with water, saturated aqueous sodium thiosulfate solution and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. The residue was purified by column chromatography on silica gel, eluting initially with dichloromethane and then with ethyl acetate:dichloromethane 1:4, to give 2-(2-heptafluoropropylbenzoxazol-5-yl)propionic acid (6.3 g).

Workup

  1. washwashed sequentially with water, saturated aqueous sodium thiosulfate solution and brine
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customthe filtrate was evaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel
  6. washeluting initially with dichloromethane

Sources & evidence

ORD record
ord-91c3f11e7554423781a8e5d46c93bb1f
Source dataset
uspto-grants-2004_03
Patent number
US06703347B2

Reaction notes

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