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

HRID 1053677Notes

Reaction equation

HRID 1053677 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]

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 7A (230 mg, 0.970 mmol), cesium carbonate (409 mg, 1.26 mmol) and 2,6-dichlorophenol (157 mg, 0.970 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 flash chromatography (hexanes/EtOAc) to give Intermediate 7B (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 flash chromatography (hexanes/EtOAc)

Sources & evidence

ORD record
ord-80ad0e735bf64f84bab9c8383fcac098
Source dataset
uspto-grants-2016_07
Patent number
US09394260B2

Reaction notes

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