Ammonia → HCID 178447825, compound

HRID 49725Notes

Reaction equation

HRID 49725 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.[NH4+].[OH-].N>C1COCC1.[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 4

HCID 222AmmoniaHCID 14923Ammonium HydroxideHCID 178447814HCID 178447814, compoundHCID 178447816HCID 178447816, compound

Product 1

HCID 178447825HCID 178447825, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

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, 10.0 g (30.6 mmol) in THF was stirred with zinc dust (10 g, 153 mmol) and aqueous 30% NH4OH at ambient temperature. After 27 h, GC analysis showed that the mixture contained <1% of the starting material. 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 8.6 g. GC analysis of the product showed that it contained 0.9% 1,1,2,2-tetrafluoro-6-(trans-4-propylcyclohexyl)-1,2-dihydronaphthalene, 13.4% 1,2,4-trifluoro-6-(trans-4-propylcyclohexyl)naphthalene, and 82% 1,2-difluoro-6-(trans-4-propylcyclohexyl)naphthalene. This example shows that when ammonia is not buffered to reduce the pH, more by-products are formed compared to the reaction in which buffered ammonia is used (Example 8).

Workup

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

Sources & evidence

ORD record
ord-5434c5f770ff41ef8eda6c5ff4dd929f
Source dataset
uspto-grants-2004_03
Patent number
US06706933B2

Reaction notes

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