Hydrochloric Acid → HCID 22030888, compound

HRID 454148Notes

Reaction equation

HRID 454148 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=1[C:24]([F:27])([F:26])[F:25])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.ClC1C=CC([CH2:35][C:36]#[N:37])=CC=1.Cl>CN(C=O)C>[CH2:7]([O:14][C:15]1[C:16]([C:24]([F:25])([F:26])[F:27])=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[C:19]([CH2:35][C:36]#[N:37])[CH:20]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2415824-Chlorobenzyl cyanideHCID 219520843-(Trifluoromethyl)-4-(benzyloxy)nitrobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 22030888HCID 22030888, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-10 °C

Procedure

Potassium tert-butoxide (3.94 g, 35.4 mmol) was dissolved in anhydrous DMF (15 ml) and a mixture of 2-benzyloxy-5-nitro-trifluoromethylbenzene (3.5 g, 16.1 mmol) and 4-chlorophenylacetonitrile (2.96 g, 17.7 mmol) in DMF (20 ml) was added over 30 minutes keeping the temperature at −15° C. The mixture was stirred at −10° C. for 1 hour, then poured into 1M hydrochloric acid (150 ml) and the product extracted with dichloromethane (2×100 ml). The organic extracts were dried (MgSO4) and purified by silica column chromatography eluting with dichloromethane/hexane (1/1) to give 5-benzyloxy-2-nitro-4-(trifluoromethyl)phenylacetonitrile (5.2 g, 77%).

Workup

  1. additionwas added over 30 minutes
  2. customat −15° C
  3. extractionthe product extracted with dichloromethane (2×100 ml)
  4. dry with materialThe organic extracts were dried (MgSO4)
  5. custompurified by silica column chromatography
  6. washeluting with dichloromethane/hexane (1/1)

Sources & evidence

ORD record
ord-e1d52b3644ed401ba407f4c15ff180bf
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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