HCID 17952680, compound → HCID 17952821, compound

HRID 1394639Notes

Reaction equation

HRID 1394639 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:25])=[C:6]([CH:8]([C:10]2[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[CH:13]=[C:12]([CH:19]([CH3:21])[CH3:20])[C:11]=2[O:22][CH2:23][CH3:24])[OH:9])[CH:7]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl.CCOCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:25])=[C:6]([C:8]([C:10]2[CH:15]=[C:14]([CH:16]([CH3:17])[CH3:18])[CH:13]=[C:12]([CH:19]([CH3:20])[CH3:21])[C:11]=2[O:22][CH2:23][CH3:24])=[O:9])[CH:7]=1

Participants

5

Reactant 2

HCID 17952680HCID 17952680, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 17952821HCID 17952821, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

(5-Bromo-2-fluoro-phenyl)-(2-ethoxy-3,5-diisopropyl-phenyl)-methanol (1.88 g, 4.6 mmol) was dissolved in dichloromethane (5 ml) and added to a suspension of pyridinium chlorochromate (1.1 g, 5.1 mmol) in dichloromethane (20 ml). After stirring at ambient temperature under and atmosphere of nitrogen for 4 h the reaction was diluted with ether (50 mL) and filtered through a plug of florosil. The remaining solvent was evaporated to yield (5-bromo-2-fluoro-phenyl)-(2-ethoxy-3,5-diisopropyl-phenyl)-methanone as yellow crystals (1.75 g, 94%). 1H NMR (250 MHz, CDCl3): δ 7.81 (dd, 1H, J=3.1, J=6.9), 7.62 (m, 1H), 7.33 (d, 1H, J=2.5), 7.28 (d, 1H, J=2.5), 7.02 (dd, 1H, J=11.2, J=9.4), 3.67 (q, 2H, J=6.9), 3.34 (m, 1H), 2.95 (m, 1H), 1.31 (s, 3H), 1.28 (s, 6H), 1.25 (s, 3H), 1.02 (t, 3H, J=6.9). MS [EI+] 407, 409 (M+H)+.

Workup

  1. filtrationfiltered through a plug of florosil
  2. customThe remaining solvent was evaporated

Sources & evidence

ORD record
ord-275cc3f2a72b4d628ee11d88f527c7dd
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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