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

2,6-Dichlorophenol → (R)-tert-butyl 1-(2,6-dichlorophenoxy)propan-2-ylcarbamate

HRID 1844400
Notes
Print preview

Reaction equation

HRID 1844400 reaction equation
Br[CH2:2][C@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=1[OH:27]>CC(C)=O>[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=1[O:27][CH2:2][C@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 68992,6-DichlorophenolHCID 10796Cesium carbonateHCID 57081792(R)-tert-butyl 1-bromopropan-2-ylcarbamate

Product 1

HCID 86731077(R)-tert-butyl 1-(2,6-dichlorophenoxy)propan-2-ylcarbamateYield 32.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Intermediate 5A (230 mg, 0.966 mmol), cesium carbonate (409 mg, 1.256 mmol) and 2,6-dichlorophenol (157 mg, 0.966 mmol) were heated in acetone (1 mL) under microwave irradiation at 100° C. for 30 min. The solvents were removed and CH2Cl2 was added. The organic phase was washed with H2O, dried over Na2SO4, filtered and concentrated. The colorless oil was purified by ISCO (hexanes/EtOAc) to give 100 mg of Intermediate 5B (100 mg, 0.312 mmol, 32.3% yield). LC-MS 219.9 (M-Boc+H), RT=2.23 min (Method B).

Workup

  1. customThe solvents were removed
  2. additionCH2Cl2 was added
  3. washThe organic phase was washed with H2O
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe colorless oil was purified by ISCO (hexanes/EtOAc)

Sources & evidence

ORD record
ord-1dd76d0f6d97401c82f381245b6df9b7
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08946430B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes