Hydrochloric Acid → HCID 57983386, compound

HRID 2078325Notes

Reaction equation

HRID 2078325 reaction equation
Cl.[Br:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:21])([CH3:20])[C:8](=[O:19])[C:9](C(OCC)=O)=[C:10]2[OH:13])=[CH:5][CH:4]=1>C(O)(C(F)(F)F)=O>[Br:2][C:3]1[CH:12]=[C:11]2[C:6](=[CH:5][CH:4]=1)[C:7]([CH3:21])([CH3:20])[C:8](=[O:19])[CH:9]=[C:10]2[OH:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67099861HCID 67099861, compound

Product 1

HCID 57983386HCID 57983386, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
80 °C

Procedure

Concentrated aqueous HCl (36.5-37.5%, 10 mL) was added to a solution of ethyl 7-bromo-1-hydroxy-4,4-dimethyl-3-oxo-3,4-dihydronaphthalene-2-carboxylate (1.40 g, 4 mmol) in TFA (10 mL). The mixture was heated to 80° C. for 18 hours. The solvent was then removed under reduced pressure, and the residue was rinsed with water and diethyl ether. The remaining solids were dried in vacuo at 50° C. to afford the title compound in 70% yield. 1H-NMR (300 MHz, DMSO-d6) δ ppm 7.98 (1H, d, J=1.9 Hz), 7.75 (1H, dd, J=2.0, 8.5 Hz), 7.67 (1H, br. d, J˜8.0 Hz), 5.64 (1H, s), 2.51 (6H, m). MS (m/z not observed).

Workup

  1. customThe solvent was then removed under reduced pressure
  2. washthe residue was rinsed with water and diethyl ether
  3. customThe remaining solids were dried in vacuo at 50° C.

Sources & evidence

ORD record
ord-797be1b8f6c4414da9513405686e9bdf
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

Loading…