Ammonium Chloride → HCID 178447832, compound

HRID 375783Notes

Reaction equation

HRID 375783 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-propylcyclohexyl)-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-trifluorobenzene 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-fda1d91d0a1a47f3abfa1ad042da2448
Source dataset
uspto-grants-1996_01
Patent number
US05487845

Reaction notes

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