2-(2,3-Dimethylphenoxy)ethanol → 2-(2,3-Dimethylphenoxy)ethyl 5-bromo-3,4-dihydroquinoline-1(2H)-carboxylate

HRID 2175228Notes

Reaction equation

HRID 2175228 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][N:7]2[C:12](Cl)=[O:13].[CH3:15][C:16]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:17]=1[O:18][CH2:19][CH2:20][OH:21].CC(C)([O-])C.[K+]>C(Cl)Cl>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][N:7]2[C:12]([O:21][CH2:20][CH2:19][O:18][C:17]1[CH:22]=[CH:23][CH:24]=[C:25]([CH3:26])[C:16]=1[CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 195937292-(2,3-Dimethylphenoxy)ethanolHCID 23665647Potassium tert-butoxideHCID 867125795-Bromo-3,4-dihydroquinoline-1(2H)-carbonyl chloride

Product 1

HCID 709828952-(2,3-Dimethylphenoxy)ethyl 5-bromo-3,4-dihydroquinoline-1(2H)-carboxylateYield 69.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-bromo-3,4-dihydroquinoline-1(2H)-carbonyl chloride (0.05 g, 0.182 mmol), 2-(2,3-dimethylphenoxy)ethanol (0.038 g, 0.228 mmol) and TEA (0.076 mL, 0.546 mmol) in DCM (1.5 mL) was stirred at room temperature for 16 h. To the mixture was then added potassium tert-butoxide (1 M in THF, 0.364 mL, 0.364 mmol) and the resulting mixture was stirred at room temperature for 24 h before being quenched with water. The organic layer was separated and the aqueous phase was extracted with DCM. The combined organic layers were dried over anhydrous MgSO4 and concentrated in vacuo to provide the crude material. The crude material was purified by flash chromatography (0-50% ethyl acetate/hexanes) to afford the title compound (51 mg, 69.3% yield). LCMS, [M+Na]+=427.9.

Workup

  1. custombefore being quenched with water
  2. customThe organic layer was separated
  3. extractionthe aqueous phase was extracted with DCM
  4. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. customto provide the crude material
  7. customThe crude material was purified by flash chromatography (0-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-7dee1b14971b4a65935b2b27615714ed
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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