Sodium Hydroxide → HCID 15389832, compound

HRID 1756704Notes

Reaction equation

HRID 1756704 reaction equation
O.O.Cl[Sn]Cl.[N+:6]([C:9]1[CH:10]=[C:11]([C:15]2([F:33])[C:18]([F:20])([F:19])[C:17]([F:22])([F:21])[C:16]2([F:32])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-])=O)[CH:24]=2)[CH:12]=[CH:13][CH:14]=1)([O-])=O.[BH4-].[Na+].[OH-].[Na+]>C(O)C.CCOCC.O>[NH2:29][C:25]1[CH:24]=[C:23]([C:16]2([F:32])[C:17]([F:21])([F:22])[C:18]([F:19])([F:20])[C:15]2([F:33])[C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([NH2:6])[CH:10]=2)[CH:28]=[CH:27][CH:26]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 4311764Sodium borohydrideHCID 15389831HCID 15389831, compound

Product 1

HCID 15389832HCID 15389832, compoundYield 93.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of SnCl2.2H2O (83.0 g) and 1,2-bis(meta-nitrophenyl)hexafluorocyclobutane (15.0 g) in 300 mL of ethanol was added NaBH4 (1.5 g) at room temperature over 20 minutes. After the addition was complete, the reaction mixture was stirred at room temperature for 3 hours and at 60° C. for one hour, and then poured into a mixture water and ether (500 mL/500 mL) and treated with NaOH solution. The ether layer was separated and aqueous layer was extracted with ether (2×300 mL). The combined ether layers were washed with NaOH solution and dried over MgSO4. After removal of the solvent, residue (13.8 g) was purified by bulb-to-bulb distillation (ca. 170° C./0.05 mmHg) twice to give 12.0 g of viscous product. 19F NMR: major isomer: -125.0 (dm J=222 Hz, 2F), -125.9 (dm, J=dm, J 222 Hz, 2F), -160.3 (s, 2F). minor isomer: -122.1 (dd, J=225.1 Hz, J=3.4 Hz, 2F), -128.7 (dd, J=255.1 Hz, J=2.4 Hz, 2F), -165.0 (s, 2F); 1H NMR: major isomer: 7.22 (t, J=7.8 Hz, 2H), 6.96 (d, J=7.8 Hz, 2H), 6.86 (s, 2H), 6.77 (dm, J=8.1 Hz, 2H), 3.76 (s, 4H); minor isomer: 7.04 (t, J=7.1 Hz, 2H), 6.63 (d, J=6.6 Hz, 2H), 6.58 (m, 4H), 3.66 (s, 4H). Anal: Calcd for C16H12F6N2 : C, 55.50; H, 3.49; F, 32.92; N, 8.09. Found: C, 55.47; H, 3.71; F, 31.12; N, 7.90.

Workup

  1. additionAfter the addition
  2. customThe ether layer was separated
  3. extractionaqueous layer was extracted with ether (2×300 mL)
  4. washThe combined ether layers were washed with NaOH solution
  5. dry with materialdried over MgSO4
  6. customAfter removal of the solvent, residue (13.8 g)
  7. distillationwas purified by bulb-to-bulb distillation (ca. 170° C./0.05 mmHg) twice

Sources & evidence

ORD record
ord-e3afdb09867c412e8b04611cac43ee69
Source dataset
uspto-grants-1995_08
Patent number
US05442030

Reaction notes

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