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Iodine → (+/-)-N-[2-chloro-3-[[4-chloro-3-(trifluoromethyl)phenyl]hydroxymethyl]phenyl]acetamide

HRID 351565
Notes
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Reaction equation

HRID 351565 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:3]=1.II.[Cl:15][C:16]1[C:21]([CH:22]=[O:23])=[CH:20][CH:19]=[CH:18][C:17]=1[NH:24][C:25](=[O:27])[CH3:26].[NH4+].[Cl-]>C1COCC1>[Cl:15][C:16]1[C:21]([CH:22]([C:2]2[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:3]=2)[OH:23])=[CH:20][CH:19]=[CH:18][C:17]=1[NH:24][C:25](=[O:27])[CH3:26]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 807IodineHCID 25517Ammonium ChlorideHCID 679594-Bromo-2-chloro-alpha,alpha,alpha-trifluorotolueneHCID 22312916N-(2-chloro-3-formylphenyl)acetamide

Product 1

HCID 22312922(+/-)-N-[2-chloro-3-[[4-chloro-3-(trifluoromethyl)phenyl]hydroxymethyl]phenyl]acetamideYield 74.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
32.5 °C

Procedure

A solution of 4-bromo-1-chloro-2-(trifluoromethyl)benzene (0.165 mol) in THF (30 ml) was added dropwise under N2 flow to a suspension of Mg (0.181 mol) and a crystal of I2 in THF (20 ml). The mixture was stirred at 30-35° C. for 2.5 hours and then cooled to 10° C. The mixture was added dropwise at 5° C. under N2 flow to a solution of N-(2-chloro-3-formylphenyl)acetamide (0.0788 mol) in THF (500 ml). The mixture was stirred at RT for 3 hours, poured out into ice and NH4Cl, and extracted with EtOAc. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography (eluent: CH2Cl2/CH3OH 98.5/1.5). The pure fractions were collected and the solvent was evaporated, yielding 22.2 g (74%) of (±)-N-[2-chloro-3-[[4-chloro-3-(trifluoromethyl)phenyl]hydroxymethyl]phenyl]acetamide (interm. 25).

Workup

  1. temperaturecooled to 10° C
  2. stirringThe mixture was stirred at RT for 3 hours
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was purified by column chromatography (eluent: CH2Cl2/CH3OH 98.5/1.5)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a8c85c4517e84f8b87dbea36c6db3b69
Source dataset
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06743792B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes