Ammonium Chloride → HCID 178447825, compound

HRID 1282450Notes

Reaction equation

HRID 1282450 reaction equation
[F:1][C:2]1(F)[C:11]2[C:6](=[CH:7][C:8]([C@H:12]3[CH2:17][CH2:16][C@H:15]([CH2:18][CH2:19][CH3:20])[CH2:14][CH2:13]3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]1(F)[F:21].FC1(F)C2C(=CC([C@H]3CC[C@H](CCC)CC3)=CC=2)C(F)=CC1F.[Cl-].[NH4+]>C1COCC1.[NH4+].[OH-].[Zn]>[F:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C@H:12]3[CH2:13][CH2:14][C@H:15]([CH2:18][CH2:19][CH3:20])[CH2:16][CH2:17]3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[F:21]

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 178447814HCID 178447814, compoundHCID 178447816HCID 178447816, compound

Product 1

HCID 178447825HCID 178447825, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolventHCID 14923Ammonium HydroxideSolvent

Procedure

A mixture of 1,1,2,2-tetrafluoro-6-(trans-4-propylcyclohexyl)-1,2-dihydronaphthalene and 1,1,2,4-tetrafluoro-6-(trans-4-propylcyclohexyl)-1,2-dihydronaphthalene, 25.6 g (78.4 mmol) in THF was stirred at ambient temperature with zinc dust (25.0 g, 382 mmol) and a solution containing ammonium chloride dissolved in aqueous 30% NH4OH. The reaction was terminated after 48 h. The mixture was filtered, and the zinc was washed with hexanes. The filtrate was transferred to a separatory funnel, the phases were separated, and the solvent was evaporated from the organic phase. The weight of product recovered was 21.9 g. GC analysis of the product showed that it contained 0.2% 1,1,2,2-tetrafluoro-6-(trans-4-propylcyclohexyl)-1,2-dihydronaphthalene, 2.1% 1,2,4-trifluoro-6-(trans-4-propylcyclohexyl)naphthalene, and 93.1% 1,2-difluoro-6-(trans-4-propylcyclohexyl)naphthalene.

Workup

  1. customThe reaction was terminated after 48 h
  2. filtrationThe mixture was filtered
  3. washthe zinc was washed with hexanes
  4. customThe filtrate was transferred to a separatory funnel
  5. customthe phases were separated
  6. customthe solvent was evaporated from the organic phase
  7. customThe weight of product recovered

Sources & evidence

ORD record
ord-dc2f3d9882e14956bef22317d0354ff3
Source dataset
uspto-grants-2002_09
Patent number
US06455744B1

Reaction notes

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