Benzyl Bromide → HCID 18433467, compound

HRID 2099593Notes

Reaction equation

HRID 2099593 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=2)[CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C)C=O>[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:16]=2)[CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 18536180tert-Butyl (7-hydroxynaphthalen-1-yl)carbamate

Product 1

HCID 18433467HCID 18433467, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (7-hydroxy-naphthalen-1-yl)-carbamic acid tert-butyl ester (5.11 g, 19.7 mmol) and potassium carbonate (3.26 g, 23.6 mmol) in N,N-dimethylformamide is added benzyl bromide (3 mL, 4.31 g, 25.2 mmol) slowly. The mixture is then stirred at room temperature over night and poured into ice-water (150 mL). The resulting mixture is extracted with ethyl acetate (4×100 mL) and the organic portions are combined, washed with water and brine, dried over sodium sulfate, concentrated and purified by silica gel chromatography (Hexanes/EtOAc=15/1) to give (7-benzyloxy-naphthalen-1-yl)-carbamic acid tert-butyl ester (5.93 g, 86.3%); 1H NMR 400 Hz (CDCl3) δ1.60 (s, 9H), 5.22 (s, 2H), 6.63 (br, 1H), 7.27 (m, 2H), 7.38 (m, 2H), 7.45 (m, 2H), 7.44 (d, J=7.44 Hz, 2H), 7.61 (d, J=8.11 Hz, 1H), 7.80 (m, 2H); MS m/z (M+Na+) 372.10.

Workup

  1. extractionThe resulting mixture is extracted with ethyl acetate (4×100 mL)
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (Hexanes/EtOAc=15/1)

Sources & evidence

ORD record
ord-f4511eb2b8594be0aec0cb76838e9153
Source dataset
uspto-grants-2009_08
Patent number
US07569593B2

Reaction notes

Loading…