1-Bromo-2-Chloroethane → HCID 10892606, compound

HRID 1171410Notes

Reaction equation

HRID 1171410 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([OH:19])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][CH2:28][Cl:29].C(OCC)(=O)C>C(#N)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([O:19][CH2:27][CH2:28][Cl:29])=[CH:11][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 78491-Bromo-2-ChloroethaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 10923237tert-Butyl (4-hydroxynaphthalen-1-yl)carbamate

Product 1

HCID 10892606HCID 10892606, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-tert-butyloxycarbonyl-4-amino-1-naphthol (2.0 g, 7.72 mmol), potassium carbonate (5.34 g, 38.6 mmol) and 1-bromo-2-chloroethane (1.28 ml, 15.4 mmol) are heated to 80° C. in anhydrous acetonitrile (40 ml) under a nitrogen atmosphere for 1 day. The mixture is poured into ethyl acetate (250 ml) and washed with water (500 ml). The aqueous layer is re-extracted with ethyl acetate (2×100 ml), the organic layers combined and dried over anhydrous sodium sulfate. The organic layers are evaporated to dryness and the residue purified by column chromatography on silica gel eluted with 20% ethyl acetate in hexanes to give [4-(2-chloro-ethoxy)-naphthalen-1-yl]-carbamic acid tert-butyl ester (1.448 g).

Workup

  1. washwashed with water (500 ml)
  2. extractionThe aqueous layer is re-extracted with ethyl acetate (2×100 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe organic layers are evaporated to dryness
  5. customthe residue purified by column chromatography on silica gel
  6. washeluted with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-ced09f4852b54005b1322b2e5a07cd7d
Source dataset
uspto-grants-2010_11
Patent number
US07829560B2

Reaction notes

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