HCID 86603988, compound → 3-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

HRID 2218759Notes

Reaction equation

HRID 2218759 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([B:11]2[O:15][C:14]([CH3:17])([CH3:16])[C:13]([CH3:19])([CH3:18])[O:12]2)[CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.FC1C=C([N+]([O-])=O)C=C(I)C=1>[Pd].C(O)C>[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([B:11]2[O:15][C:14]([CH3:16])([CH3:17])[C:13]([CH3:19])([CH3:18])[O:12]2)[CH:3]=1

Participants

4

Reactant 1

HCID 86603988HCID 86603988, compound

Product 1

HCID 597700393-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Combine 1-fluoro-3-iodo-5-nitrobenzene 2-(3-Fluoro-5-nitro-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (940 mg, 3.5 mmol), 5% palladium on carbon (˜60% H2O, 200 mg), and anhydrous ethanol (25 mL). Purge and fill the reaction vessel with hydrogen three times. Stir the reaction mixture under 1 atm of hydrogen. When the reaction is complete by LCMS, filter the reaction mixture through celite to remove the catalyst and wash the filter cake with ethanol. Strip to dryness and purify the crude product by flash chromatography (25% ethyl acetate/hexanes) and combine product fractions. Strip to dryness to provide the crude product. LCMS (APCI-pos): mass 238.2 (M+1), Purity by LCMS (UV area percent): 85%. 1HNMR (CDCl3, 400 MHz): δ6.88-6.83 (m, 2H), 6.47-6.43 (m, 1H), 3.55-3.9 (bs, 2H), 1.32 (s, 12H)

Workup

  1. customPurge
  2. filtrationfilter the reaction mixture through celite
  3. customto remove the catalyst
  4. washwash the filter cake with ethanol
  5. customStrip to dryness and purify the crude product by flash chromatography (25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f83c304c43cb40e5aff1ec95e0e7e9d0
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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