Hydrochloric Acid → 4-Amino-4'-n-octyl-2',3',5',6'-tetrafluorobiphenyl

HRID 601454Notes

Reaction equation

HRID 601454 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:22]([F:23])=[C:21]([F:24])[C:20](F)=[C:19]([F:26])[C:18]=2[F:27])=[CH:13][CH:12]=1.Cl>CCOCC>[NH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[C:18]([F:27])=[C:19]([F:26])[C:20]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[C:21]([F:24])[C:22]=2[F:23])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 159386172',3',4',5',6'-Pentafluoro[1,1'-biphenyl]-4-ylamineHCID 178506867HCID 178506867, compound

Product 1

HCID 159386224-Amino-4'-n-octyl-2',3',5',6'-tetrafluorobiphenyl

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

n-Octyllithium in dry ether (9.5 mL) was added slowly to a solution of 4-amino-2′,3′,4′,5′,6′-pentafluorobiphenyl (1.5 g, 5.79 mmol, Example 9) in dry ether (100 mL) at −78° C. The solution was stirred at this temperature for 2 hours and then allowed to warm to room temperature over a period of 5 hours. Hydrochloric acid (3M, 100 mL) was added and a white solid was precipitated from the solution. The solid was filtered and dried. After sublimation, 4-amino-4′-n-octyl-2′,3′,5′,6′-tetrafluorobiphenyl was obtained as a white solid (1.2 g, 63% yield).

Workup

  1. customa white solid was precipitated from the solution
  2. filtrationThe solid was filtered
  3. customdried

Sources & evidence

ORD record
ord-a3851edf7f04442f9808ef4b8d7676e7
Source dataset
uspto-grants-2011_03
Patent number
US07902363B2

Reaction notes

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