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

HRID 1641257Notes

Reaction equation

HRID 1641257 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([OH:18])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:21][CH2:22][CH2:23][Cl:24].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][CH2:21][CH2:22][CH2:23][Cl:24])=[CH:10][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

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-78386b14a47145dc98f83d0d50d5d7e7
Source dataset
uspto-grants-2012_02
Patent number
US08114873B2

Reaction notes

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