HCID 67126235, compound → 6-Chloro-7-fluoro-3-methylnaphthalen-1-ol

HRID 514102Notes

Reaction equation

HRID 514102 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([CH3:17])=[CH:11][C:12]([O:14]CC)=O)[CH:5]=[CH:6][C:7]=1[F:8]>S(=O)(=O)(O)O.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][C:7]=1[F:8])[C:12]([OH:14])=[CH:11][C:10]([CH3:17])=[CH:9]2

Participants

4

Reactant 1

HCID 67126235HCID 67126235, compound

Product 1

HCID 671261486-Chloro-7-fluoro-3-methylnaphthalen-1-olYield 19.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of ethyl 4-(3-chloro-4-fluorophenyl)-3-methylbut-2-enoate (9.7 g, 37.8 mmol) in concentrated sulfuric acid (40 mL) was stirred at 50° C. overnight. The reaction mixture was poured onto ice and diluted with water and extracted with ethyl acetate. The organic layer was concentrated and purified by flash column chromatography (silica gel, ethyl acetate/hexanes) to give a pale yellow solid (1.57 g). 1H-NMR: 400 MHz, (CDCl3) δ: 7.83 (d, J=10.4 Hz, 1H), 7.75 (d, J=7.2 Hz, 1H), 7.11 (s, 1H), 6.67 (s, 1H), 2.42 (s, 3H).

Workup

  1. additionThe reaction mixture was poured onto ice
  2. extractionextracted with ethyl acetate
  3. concentrationThe organic layer was concentrated
  4. custompurified by flash column chromatography (silica gel, ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-db69d8db1fe649929295841ccf6acb45
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

Loading…