Hexachloroethane → 2-(4-(Cyclopropylmethoxy)-3,5-difluorophenyl)-1,3-benzoxazol-6-ol

HRID 2277198Notes

Reaction equation

HRID 2277198 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[C:22]([F:23])=[CH:21][C:9]([C:10]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]=3[OH:20])=O)=[CH:8][C:7]=2[F:24])[CH2:3][CH2:2]1.ClC(Cl)(Cl)C(Cl)(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C(#N)C>[CH:1]1([CH2:4][O:5][C:6]2[C:22]([F:23])=[CH:21][C:9]([C:10]3[O:20][C:14]4[CH:15]=[C:16]([OH:19])[CH:17]=[CH:18][C:13]=4[N:12]=3)=[CH:8][C:7]=2[F:24])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6214HexachloroethaneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 867312594-(cyclopropylmethoxy)-N-(2,4-dihydroxyphenyl)-3,5-difluorobenzamide

Product 1

HCID 867312582-(4-(Cyclopropylmethoxy)-3,5-difluorophenyl)-1,3-benzoxazol-6-olYield 53.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(cyclopropylmethoxy)-N-(2,4-dihydroxyphenyl)-3,5-difluorobenzamide (3.78 g), hexachloroethane (6.67 g) and triphenylphosphine (7.39 g) in acetonitrile (50 mL) was added triethylamine (3.42 mL), and the mixture was stirred at room temperature for 15 min, and then with heating at 80° C. for 1 hr. The reaction mixture was filtered, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (1.92 g).

Workup

  1. temperaturewith heating at 80° C. for 1 hr
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-12472fa7466f4911b0df55692bf85819
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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