Sodium Hydroxide → HCID 58976138, compound

HRID 601015Notes

Reaction equation

HRID 601015 reaction equation
O.O.[Sn](Cl)(Cl)(Cl)Cl.[F:8][CH:9]([F:24])[O:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][C:12]=1[O:20][CH:21]([CH3:23])[CH3:22].[OH-].[Na+]>Cl.C(OCC)(=O)C>[F:8][CH:9]([F:24])[O:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:12]=1[O:20][CH:21]([CH3:22])[CH3:23]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 58976196HCID 58976196, compoundHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 58976138HCID 58976138, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To tin chloride dihydrate (5.46 g, 24.2 mmol) in concentrated HCl (7 mL) at 0° C. was added 1-difluoromethoxy-2-isopropoxy-4-nitro-benzene (1.712 g, 6.92 mmol) in ethyl acetate (7 mL) and the reaction was stirred for 1 h. The reaction was adjusted to ˜pH7 with NaOH and was filtered through Celite, washing with ethyl acetate. The filtrate was separated and the aqueous phase was back extracted with ethyl acetate. The combined organic phase was washed with brine, dried (sodium sulfate) and evaporated. Purification by flash chromatography (SiO2) eluted with 2:8 ethyl acetate:hexanes provided 4-difluoromethoxy-3-isopropoxy-phenylamine (0.55 g, 37% yield, 57% yield based on recovered starting material) as an orange oil. 1H-NMR (CDCl3, 500 MHz) 6.94 (d, 1H), 6.41 (t, 1H), 6.31 (dd, 1H), 6.23 (d, 1H), 4.47 (m, 1H), 1.33 (d, 6H) ppm; MS (FIA) 218.2 (M+H); HPLC (Method A) 2.853 min.

Workup

  1. filtrationwas filtered through Celite
  2. washwashing with ethyl acetate
  3. customThe filtrate was separated
  4. extractionthe aqueous phase was back extracted with ethyl acetate
  5. washThe combined organic phase was washed with brine
  6. dry with materialdried (sodium sulfate)
  7. customevaporated
  8. customPurification by flash chromatography (SiO2)
  9. washeluted with 2:8 ethyl acetate

Sources & evidence

ORD record
ord-56fad6d83c06459b8b0d6540d5ed2c4b
Source dataset
uspto-grants-2011_03
Patent number
US07902239B2

Reaction notes

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