Ammonium Chloride → HCID 178447832, compound

HRID 1684474Notes

Reaction equation

HRID 1684474 reaction equation
C([Li])CCC.[CH2:6]([C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][C:24](Br)=[CH:23][CH:22]=3)=[C:17]([F:28])[CH:16]=2)[CH2:11][CH2:10]1)[CH2:7][CH3:8].Br[C:30]1[CH:35]=[C:34]([F:36])[C:33]([F:37])=[C:32]([F:38])[CH:31]=1.[NH4+].[Cl-]>C1COCC1.Cl[Pd]Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].[Zn+2].[Br-].[Br-]>[CH2:6]([C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[C:26]([C:30]4[CH:35]=[C:34]([F:36])[C:33]([F:37])=[C:32]([F:38])[CH:31]=4)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:17]([F:28])[CH:16]=2)[CH2:11][CH2:10]1)[CH2:7][CH3:8]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 6114091-Bromo-3,4,5-trifluorobenzeneHCID 178418339ButyllithiumHCID 178447830HCID 178447830, compound

Product 1

HCID 178447832HCID 178447832, compound

Reagents, catalysts & solvents 3

HCID 10421208Zinc bromideCatalystHCID 8028TetrahydrofuranSolvent3×HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Solvent

Procedure

25 ml of butyllithium (15% in hexane) are added dropwise at -70° C. to a solution of 15 g of 4-(trans-4-n-propyl-cyclohexyl)-2-fluoro-4'-bromobiphenyl in 50 ml of THF and a cooled solution of 4.5 g of ZnBr2 in 25 ml of THF is added after 30 min. After addition of 8.5 g of 1-bromo-3,4,5-triflurobenzene in 75 ml of THF and 0.6 g of PdCl2 -dppf, the mixture is allowed to come to room temperature. After stirring for 24 h, the mixture is poured into 100 ml of saturated NH4Cl solution and worked up as usual. 4"-(trans-4-n-Propylcyclohexyl)-2",3,4,5-tetrafluoroterphenyl is obtained, C 148 N 233 I.

Workup

  1. customto come to room temperature

Sources & evidence

ORD record
ord-6f587051d0204e2eba1e9fe05f3fdebc
Source dataset
uspto-grants-1997_06
Patent number
US05641429

Reaction notes

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