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Hydrochloric Acid → 2-(4-Ethoxyphenyl)-3,3,3-trifluoropropyl 4-fluoro-3-anilinobenzyl ether

HRID 1904978
Notes
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Reaction equation

HRID 1904978 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([C:15]([F:18])([F:17])[F:16])[CH2:13][OH:14])=[CH:8][CH:7]=1)[CH3:4].[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][C:21]=1[NH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.Cl>C1COCC1>[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][O:14][CH2:13][CH:12]([C:9]2[CH:8]=[CH:7][C:6]([O:5][CH2:3][CH3:4])=[CH:11][CH:10]=2)[C:15]([F:16])([F:17])[F:18])=[CH:22][C:21]=1[NH:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 10681171(RS)-1,1,1-trifluoro-2-(4-ethoxyphenyl)propan-3-olHCID 200366814-Fluoro-3-anilinobenzyl bromide

Product 1

HCID 145808272-(4-Ethoxyphenyl)-3,3,3-trifluoropropyl 4-fluoro-3-anilinobenzyl ether

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

Under a nitrogen atmosphere, 120 mg of sodium hydride (60% oil dispersion) was added to 10 ml of dry THF. A solution of 0.69 of 2-(4-ethoxyphenyl)-3,3,3-trifluoropropanol and 0.82 g or 4-fluoro-3-anilinobenzyl bromide in 20 ml of dry THF was then added with ice-cooling, and the reaction solution was stirred with ice-cooling for 1 hour and at room temperature for 46 hours. Thereafter, the reaction mixture was poured into ice water and adjusted to pH 6 with dilute HCl and extracted twice with diethyl ether. The ether layers were combined, washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed under a reduced pressure, and the residue was subjected to column chromatography on silica gel [eluted with n-hexane/ethyl acetate (25:1) mixture] to obtain 368 mg of the desired compound.

Workup

  1. temperaturecooling
  2. extractionextracted twice with diethyl ether
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under a reduced pressure

Sources & evidence

ORD record
ord-2bf2bc0fa39d4f94b3d38d57f68f247b
Source dataset
uspto-grants-1989_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04840971

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes