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1-Chloro-4-(trifluoromethyl)benzene → 4-(4-Trifluoromethylphenyl)morpholine

HRID 355561
Notes
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Reaction equation

HRID 355561 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.CC(C)([O-])C.[K+].[Br-].[Li+]>C1(C)C=CC=CC=1>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:3][CH:4]=1.[F:9][C:8]([F:11])([F:10])[C:5]1[CH:4]=[C:3]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:2]=[CH:7][CH:6]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 73941-Chloro-4-(trifluoromethyl)benzeneHCID 8083MorpholineHCID 82050Lithium BromideHCID 23665647Potassium tert-butoxide

Product 2

HCID 109333104-(4-Trifluoromethylphenyl)morpholineHCID 154202994-(3-(Trifluoromethyl)phenyl)morpholine

Reagents, catalysts & solvents

1
HCID 1140TolueneSolvent

Procedure

2.0 mmol of 4-chlorobenzotrifluoride, 2.4 mmol of morpholine, 2.8 mmol of potassium tert-butoxide, 0.4 mmol of lithium bromide, 1.0 mol-% (9.4 mg) of palladacycle (trans-di(μ-aceto)-bis[o[di-o-tolylphosphino)benzyl]dipalladium(II) in 10 ml of toluene are reacted according to the GWI to give 4-trifluoromethylphenylmorpholine and 3-trifluoromethylphenylmorpholine in the ratio 5:1 in 62% yield.

Sources & evidence

ORD record
ord-2218640268a64655b55ace309eaf0f6d
Source dataset
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05831128

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes