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Iodine → 2-(4-Bromo-2-chlorophenyl)-1,3-oxazole

HRID 965947
Notes
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Reaction equation

HRID 965947 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([NH:8][CH2:9][CH:10]=[O:11])=O)=[C:4]([Cl:14])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.II.C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]2[O:11][CH:10]=[CH:9][N:8]=2)=[C:4]([Cl:14])[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 807IodineHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 223137814-Bromo-2-chloro-N-(2-oxoethyl)benzamide

Product 1

HCID 223137822-(4-Bromo-2-chlorophenyl)-1,3-oxazoleYield 20%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a stirred solution of 4-bromo-2-chloro-N-(2-oxoethyl)benzamide (1.00 g, 3.617 mmol) in CH2Cl2 (30 mL) were added triphenylphosphine (1.90 g, 7.234 mmol), iodine (1.84 g, 7.234 mmol) and triethylamine (2.0 mL, 14.47 mmol) at room temperature. After 24 hour, the mixture was washed with water (20 mL), dried over MgSO4. Removal of the solvent, gave an oily recidue, which was purified by flash chromatography eluting with ethyl acetate/hexane (1/5) to give title compound (0.185 g, 20% yield).

Workup

  1. washthe mixture was washed with water (20 mL)
  2. dry with materialdried over MgSO4
  3. customRemoval of the solvent
  4. customgave an oily recidue, which
  5. customwas purified by flash chromatography
  6. washeluting with ethyl acetate/hexane (1/5)

Sources & evidence

ORD record
ord-ac43222cdd35487ebf128bdea4dbd085
Source dataset
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06951876B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes