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Diethyl Ether → Ethyl 2,6-difluoro-4-[(3-hydroxy-4-chloro-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-benzoate

HRID 1935657
Notes
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Reaction equation

HRID 1935657 reaction equation
[F:1][C:2]1[CH:12]=[C:11]([NH:13][C:14]([C:16]2[C:25]([OH:26])=[CH:24][C:23]3[C:22]([CH3:28])([CH3:27])[CH2:21][CH2:20][C:19]([CH3:30])([CH3:29])[C:18]=3[CH:17]=2)=[O:15])[CH:10]=[C:9]([F:31])[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].S(Cl)([Cl:35])(=O)=O.C(OCC)C>ClCCl>[F:1][C:2]1[CH:12]=[C:11]([NH:13][C:14]([C:16]2[C:25]([OH:26])=[C:24]([Cl:35])[C:23]3[C:22]([CH3:28])([CH3:27])[CH2:21][CH2:20][C:19]([CH3:30])([CH3:29])[C:18]=3[CH:17]=2)=[O:15])[CH:10]=[C:9]([F:31])[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24648Sulfuryl chlorideHCID 22465056Ethyl 2,6-difluoro-4-[(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-benzoate2×

Product 1

HCID 10298591Ethyl 2,6-difluoro-4-[(3-hydroxy-4-chloro-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-benzoate

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a solution ethyl 2,6-difluoro-4-[(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-benzoate (Compound C, 227 mg, 0.52 mmol) in 10 ml of anhydrous dichloromethane under nitrogen at 25° C. was added sulfuryl chloride (0.0413 ml, 0.57 mmol) and anhydrous ethyl ether (0.054 ml, 0.52 mmol). Reaction was instantaneous at 25° C. as monitored by 1H NMR. The reaction mixture was quenched with saturated NaHCO3 then extracted with ethyl acetate. The organic layer was washed with water, brine and dried over Na2SO4. The title compound was obtained as a white solid after column chromatography with ethyl acetate:hexane (1:9).

Workup

  1. customReaction
  2. customwas instantaneous at 25° C.
  3. customThe reaction mixture was quenched with saturated NaHCO3
  4. extractionthen extracted with ethyl acetate
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-6abf7bc3a4384040ac155343446acb96
Source dataset
uspto-grants-2002_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06387950B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes