Boron trifluoride etherate → 7'-Fluoro-3',4'-dihydro-2'H-spiro[[1,3]dithiolane-2,1'-naphthalene]

HRID 919191Notes

Reaction equation

HRID 919191 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=O)=[CH:4][CH:3]=1.B(F)(F)F.CCOCC.[CH2:22]([SH:25])[CH2:23][SH:24]>>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]32[S:25][CH2:22][CH2:23][S:24]3)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 8000Boron trifluoride etherateHCID 109021,2-EthanedithiolHCID 103747647-Fluoro-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 866652417'-Fluoro-3',4'-dihydro-2'H-spiro[[1,3]dithiolane-2,1'-naphthalene]Yield 100%

Procedure

Dissolved 7-fluorotetralone, 51 (10.0 g, 60.9 mmol) in 1,2-ethanedithiol (10 mL) and cooled reaction to 0° C. Boron trifluoride diethyl etherate (7.5 mL) was added dropwise. The white suspension became yellow and homogenous. The wet ice bath was removed and the reaction was warmed to ambient temperature. The reaction was then diluted with heptanes (25 mL) and poured into an ice cold solution of saturated sodium bicarbonate. The organic layer was separated, dried over sodium sulfate and concentrated to give colorless oil (14.69 g, 60.9 mmol, 100% yield). 1H NMR (400 MHz, CDCl3) δ: 7.60 (d, J=12 Hz, 1H), 6.94 (t, J=4 Hz, 1H), 6.84 (t, J=8 Hz, 1H), 3.56 (m, 2H), 3.46 (m, 2H), 2.75 (m, 2H), 2.37 (m, 2H), 1.99 (m, 2H).

Workup

  1. temperaturecooled
  2. customreaction to 0° C
  3. customThe wet ice bath was removed
  4. additionThe reaction was then diluted with heptanes (25 mL)
  5. additionpoured into an ice cold solution of saturated sodium bicarbonate
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-704e6a99e18f480d99efc16815b3c75a
Source dataset
uspto-grants-2016_03
Patent number
US09273009B2

Reaction notes

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