Carbon Tetrachloride → HCID 59350837, compound

HRID 1644748Notes

Reaction equation

HRID 1644748 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Cl:24])(Cl)(Cl)Cl.[CH2:25]([S:27]([C:30]1[CH:50]=[CH:49][C:33]([CH2:34][C:35]2[C:44]3[C:39](=[CH:40][CH:41]=[C:42]([F:45])[CH:43]=3)[CH:38]=[C:37](CO)[C:36]=2[CH3:48])=[CH:32][CH:31]=1)(=[O:29])=[O:28])[CH3:26]>O1CCCC1.C(OCC)(=O)C>[CH2:25]([S:27]([C:30]1[CH:50]=[CH:49][C:33]([CH2:34][C:35]2[C:44]3[C:39](=[CH:40][CH:41]=[C:42]([F:45])[CH:43]=3)[CH:38]=[C:37]([CH2:20][Cl:24])[C:36]=2[CH3:48])=[CH:32][CH:31]=1)(=[O:28])=[O:29])[CH3:26]

Participants

6

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 59350828HCID 59350828, compound

Product 1

HCID 59350837HCID 59350837, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of triphenylphosphine (1.10 g, 4.19 mmol), carbon tetrachloride (1.62 mL, 16.8 mmol) and tetrahydrofuran (5 mL) was stirred at room temperature for 10 minutes. A mixture of [4-(4-ethanesulfonyl-benzyl)-6-fluoro-3-methyl-naphthalen-2-yl]-methanol (780 mg, 2.09 mmol) in tetrahydrofuran (2.5 mL) was added, and the reaction mixture was stirred at 75° C. for 4 hours. The reaction mixture was cooled to room temperature, and then diluted with ethyl acetate. The resulting mixture was washed with water. The organic phase was dried over MgSO4, filtered, and concentrated. A solution of the crude product in dichloromethane was evaporated over silica gel, and the silica gel supported crude product was loaded onto an Analogix SuperFlash™ column. Flash chromatography (10%-30% ethyl acetate in hexanes) afforded 450 mg (55%) of 1-(4-ethanesulfonyl-benzyl)-3-chloromethyl-7-fluoro-2-methyl-naphthalene as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.04 (s, 1 H), 7.96-8.04 (m, 1 H), 7.76 (d, J=8.2 Hz, 2 H), 7.68-7.75 (m, 1 H), 7.41 (td, J=8.6, 2.1 Hz, 1 H), 7.30 (d, J=8.2 Hz, 2 H), 5.01 (s, 2 H), 4.63 (s, 2 H), 3.22 (q, J=7.2 Hz, 2 H), 2.47 (s, 3 H), 1.06 (t, J=7.2 Hz, 3 H). MS (ES+) cald. for C21H20CIFO2S [(M−Cl)+] 355, obsd. 355.

Workup

  1. additionwas added
  2. stirringthe reaction mixture was stirred at 75° C. for 4 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. washThe resulting mixture was washed with water
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customA solution of the crude product in dichloromethane was evaporated over silica gel

Sources & evidence

ORD record
ord-dd1960003a1348989fecbc82394831f3
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

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