Water → 6-fluoro-3,4-dihydro-2-phenyl-1(2H)-naphthalenone

HRID 22196Notes

Reaction equation

HRID 22196 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[C:7]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(C(OC)=O)[CH2:6][CH2:5]2.[Cl-].[Li+].O>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH:7]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 962WaterHCID 433294Lithium ChlorideHCID 57050899Methyl 6-fluoro-1,2,3,4-tetrahydro-1-oxo-2-phenyl-2-naphthalenecarboxylate

Product 1

HCID 139534336-fluoro-3,4-dihydro-2-phenyl-1(2H)-naphthalenoneYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

The tetralone from Step B (2.8 g, 9.4 mmole) was dissolved in 45 ml of dimethylformamide. To this solution was added lithium chloride (2.0 g, 47 mmole) and water (0.42 ml, 23 mmole). The reaction mixture was heated to 150° C. for 2.5 hrs and then cooled and partitioned between ether and water. The aqueous phase was separated and extracted three times with ether. The combined organic phases were washed once with water, dried (MgSO4), and concentrated (1.96 g, 87% yield). 1H NMR (CDCl3) δ: 8.13 (1H, dd, J=6,10 Hz), 7.31 (5H, m) 6.99 (2H, m), 3.80 (1H, m), 3.07 (2H, m), 2.43 (2H, m).

Workup

  1. temperaturecooled
  2. custompartitioned between ether and water
  3. customThe aqueous phase was separated
  4. extractionextracted three times with ether
  5. washThe combined organic phases were washed once with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated (1.96 g, 87% yield)

Sources & evidence

ORD record
ord-6ff7a09fc901415cac37fb3dec45b7b5
Source dataset
uspto-grants-1995_06
Patent number
US05428027

Reaction notes

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