Ammonium Chloride → HCID 178444424, compound

HRID 1109959Notes

Reaction equation

HRID 1109959 reaction equation
[Li].[CH2:2]([C@H:7]1[CH2:12][CH2:11][C@H:10]([CH2:13][CH2:14]I)[CH2:9][CH2:8]1)[CH2:3][CH2:4][CH2:5][CH3:6].[F:16][C:17]([F:27])([F:26])[O:18][C:19]1[CH:24]=[CH:23][C:22](Br)=[CH:21][CH:20]=1.[NH4+].[Cl-]>[Zn+2].[Br-].[Br-].Cl[Pd]Cl.C1COCC1.C1(C)C=CC=CC=1>[F:16][C:17]([F:27])([F:26])[O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:14][CH2:13][C@H:10]2[CH2:11][CH2:12][C@H:7]([CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:8][CH2:9]2)=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 5210081-Bromo-4-(trifluoromethoxy)benzeneHCID 3028194LithiumHCID 178444481HCID 178444481, compound

Product 1

HCID 178444424HCID 178444424, compound

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 10421208Zinc bromideCatalystHCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

0.7 g of lithium and 5.7 g of ZnBr2 are added at 0° to a mixture of 15.4 g of trans-4-pentylcyclohexylethyliodide and 100 ml of THF/toluene (1:4), and the reaction mixture is treated with ultrasound at 0°-10° for 4 hours. 14.8 g of 4-trifluoromethoxybromobenzene and 0.88 g of PdCl2 (dppf) are subsequently added at 5°. The mixture is allowed to warm to room temperature and is stirred for a further 16 hours. The mixture is then poured into 100 ml of saturated NH4Cl solution, and the organic phase is work ed up. After purification by chromatography and/or crystallization, 1-(4-trifluoromethoxyphenyl)-2-(trans-4-pentylcyclohexyl)-ethane is obtained.

Workup

  1. additionthe reaction mixture is treated with ultrasound at 0°-10° for 4 hours
  2. customAfter purification
  3. customby chromatography and/or crystallization

Sources & evidence

ORD record
ord-1a0516b938444f8f8ba69b2f7bc26125
Source dataset
uspto-grants-1994_06
Patent number
US05324449

Reaction notes

Loading…