HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Cesium carbonate → Tert-butyl 3-(2-fluorophenoxy)cyclohexylcarbamate

HRID 530843
Notes
Print preview

Reaction equation

HRID 530843 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3]1.[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1I.CC1C=NC2C(C=1C)=CC=C1C=2N=CC(C)=C1C.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.[Cu](I)I>[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:3]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 676731-Fluoro-2-iodobenzeneHCID 742653,4,7,8-Tetramethyl-1,10-phenanthrolineHCID 21925254tert-Butyl (3-hydroxycyclohexyl)carbamate

Product 1

HCID 67983693Tert-butyl 3-(2-fluorophenoxy)cyclohexylcarbamate

Reagents, catalysts & solvents 2

HCID 83717
Copper iodide
Catalyst
HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A reaction mixture of tert-butyl 3-hydroxycyclohexylcarbamate (4 mmol, 861 mg), 1-fluoro-2-iodobenzene (5 mmol, 585 4), copper iodide (0.4 mmol, 76 mg), 3,4,7,8-tetramethyl-1,10-phenanthroline (0.8 mmol, 190 mg) and cesium carbonate (10 mmol, 3.26 g) in toluene (5 mL) was stirred at 110° C. for overnight under argon. The reaction mixture was cooled to room temperature and filtered through celite. The filtrate was concentrated. The mixture was purified by silica gel column chromatography. The product, tert-butyl 3-(2-fluorophenoxy)cyclohexylcarbamate, was eluted off the column using 15% EtOAc in Hexane.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through celite
  3. concentrationThe filtrate was concentrated
  4. customThe mixture was purified by silica gel column chromatography
  5. washThe product, tert-butyl 3-(2-fluorophenoxy)cyclohexylcarbamate, was eluted off the column

Sources & evidence

ORD record
ord-de94344fee0c49f68e3aaabeaac80058
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09351965B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes