Nitrilooxonium tetrafluoroborate → HCID 69385839, compound

HRID 860969Notes

Reaction equation

HRID 860969 reaction equation
[F:1][B-](F)(F)F.N#[O+].[CH3:8][O:9][C:10](=[O:33])[CH2:11][C:12]1[CH:17]=[C:16]([Br:18])[C:15]([O:19][C:20]2[CH:25]=[C:24]([CH:26]([CH3:28])[CH3:27])[C:23]([O:29][CH3:30])=[C:22](N)[CH:21]=2)=[C:14]([Br:32])[CH:13]=1>ClCCl>[CH3:8][O:9][C:10](=[O:33])[CH2:11][C:12]1[CH:17]=[C:16]([Br:18])[C:15]([O:19][C:20]2[CH:25]=[C:24]([CH:26]([CH3:28])[CH3:27])[C:23]([O:29][CH3:30])=[C:22]([F:1])[CH:21]=2)=[C:14]([Br:32])[CH:13]=1

Participants

4

Reactant 2

HCID 11137142Nitrilooxonium tetrafluoroborateHCID 69388013HCID 69388013, compound

Product 1

HCID 69385839HCID 69385839, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of nitrosonium tetrafluoroborate (121 mg, 1.03 mmol) in dichloromethane (10 mL) was cooled to 0° C. and methyl[3,5-dibromo-4-(3-amino-5-isopropyl-4-methoxy-phenoxy)phenyl]acetate (457 mg, 0.94 mmol) was added. The reaction mixture was stirred at 0° C. for one hour. Dichloromethane was removed by flushing of nitrogen gas and o-xylene (10 mL) was added to the residue. The reaction mixture was heated at reflux for one hour and the organic phase concentrated in vacuo. The residue was purified on column (silica gel, n-heptane/ethyl acetate, gradient elution from 98:2 to 60:40) to give 205 mg (44%) of methyl[3,5-dibromo-4-(3-fluoro-5-isopropyl-4-methoxyphenoxy)phenyl]acetate.

Workup

  1. customDichloromethane was removed
  2. customby flushing of nitrogen gas and o-xylene (10 mL)
  3. additionwas added to the residue
  4. temperatureThe reaction mixture was heated
  5. temperatureat reflux for one hour
  6. concentrationthe organic phase concentrated in vacuo
  7. customThe residue was purified on column (silica gel, n-heptane/ethyl acetate, gradient elution from 98:2 to 60:40)

Sources & evidence

ORD record
ord-44f0f73b3d204d049d1aee357445c6d5
Source dataset
uspto-grants-2006_12
Patent number
US07153997B2

Reaction notes

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