4-Bromophenol → tert-butyl N-[2-(4-bromophenoxy)ethyl]-N-methylcarbamate

HRID 626158Notes

Reaction equation

HRID 626158 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH3:12])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[Br:13][C:14]1[CH:19]=[CH:18][C:17](O)=[CH:16][CH:15]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([O:1][CH2:2][CH2:3][N:4]([CH3:12])[C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 78084-BromophenolHCID 11776TriphenylphosphineHCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanolHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 20785720tert-butyl N-[2-(4-bromophenoxy)ethyl]-N-methylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl 2-hydroxyethyl(methyl)carbamate (1.5 eq), 4-bromophenol (1.0 eq) and PPh3 (1.5 eq) in anhydrous THF under nitrogen was added DIAD (1.5 eq) dropwise at 0° C. The reaction was stirred at rt. for 48 h., quenched with water, and extracted with EtOAc. The extract was dried, concentrated, and purified by column chromatography to give the desired product.

Workup

  1. customquenched with water
  2. extractionextracted with EtOAc
  3. customThe extract was dried
  4. concentrationconcentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-adb1b0ada3474243baee9f854be18609
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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