1-Bromo-3-chloropropane → HCID 59553343, compound

HRID 1171389Notes

Reaction equation

HRID 1171389 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:4][CH:3]=1.Br[CH2:21][CH2:22][CH2:23][Cl:24].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[C:15]([O:14][C:13](=[O:19])[NH:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([O:1][CH2:21][CH2:22][CH2:23][Cl:24])=[CH:3][CH:4]=1)([CH3:16])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 10923237tert-Butyl (4-hydroxynaphthalen-1-yl)carbamate

Product 1

HCID 59553343HCID 59553343, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Tert-butyl (4-hydroxy-1-naphthyl)carbamate (3.93 g, 15.1 mmol), 1-bromo-3-chloropropane (5.5 g, 34.8 mmol), and K2CO3 (10.0 g, 75.8 mmol) in acetonitrile (50 ml) are heated to 80° C. with agitation for 8 h. After cooling to room temperature the mixture is filtered and concentrated under vacuum. The residue is purified by column chromatography on silica gel to yield [4-(3-chloropropoxy)-naphthalen-1-yl]-carbamic acid tert-butyl ester. 4 g, 78% is produced as an off-white solid. MS: 336.2 (M+1).

Workup

  1. filtrationis filtered
  2. concentrationconcentrated under vacuum
  3. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-da401c9b55d343159bf894eaf2bdfb20
Source dataset
uspto-grants-2010_11
Patent number
US07829560B2

Reaction notes

Loading…