1,2,3,4-Tetramethylbenzene → HCID 87429238, compound

HRID 926968Notes

Reaction equation

HRID 926968 reaction equation
[Br:1][CH2:2][S:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)=O.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([CH3:20])[C:14]=1[CH3:21].[F:22][C:23]([F:36])([F:35])[S:24]([O:27]S(C(F)(F)F)(=O)=O)(=[O:26])=[O:25]>C(OCC)C>[O-:27][S:24]([C:23]([F:36])([F:35])[F:22])(=[O:26])=[O:25].[Br:1][CH2:2][S+:3]([C:18]1[CH:17]=[C:16]([CH3:19])[C:15]([CH3:20])=[C:14]([CH3:21])[C:13]=1[CH3:12])[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 102631,2,3,4-TetramethylbenzeneHCID 67749Trifluoromethanesulfonic anhydrideHCID 12264385HCID 12264385, compound

Product 1

HCID 87429238HCID 87429238, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-((bromomethyl)sulfinyl)-4-methylbenzene (200 mg, 0.86 mmol) of example 35 was dissolved in dry diethyl ether (6 mL) under argon atmosphere. 1,2,3,4-tetramethylbenzene (0.127 g, 1.1 eq) was added to the previous solution and then the mixture was cooled to a temperature below −60° C. After stabilizing the temperature below −60° C., trifluoromethanesulfonic anhydride (0.145 mL, 1 eq) was slowly added maintaining the same temperature. After 4 hours at −60° C., the precipitate triflate salt was isolated by filtration and dried under vacuum. 0.358 g (83%) of the desired product was obtained as a white solid. mp: 136-138° C. 1H NMR (CDCl3, 400 MHz): δ 7.81 (2H, d, J=8.4 Hz), 7.71 (1H, s), 7.46 (2H, d, J=8.2 Hz), 5.69 (2H, ABQ, J=10.0 Hz), 2.50 (3H, s), 2.43 (3H, s), 2.42 (3H, s), 2.27 (3H, s), 2.26 (3H, s). 13C NMR (CDCl3, 100 MHz): δ 146.5, 143.9, 138.9, 138.8, 136.7, 132.2, 130.6, 126.9, 120.4, 118.5, 35.2, 21.6, 20.8, 17.4, 16.88, 16.81. FT-IR (KBr): 3027, 2954, 1492, 1450, 1400, 1288, 1245, 1220, 1162, 1147, 1027 cm−1.

Workup

  1. temperaturethe mixture was cooled to a temperature below −60° C
  2. additionwas slowly added
  3. temperaturemaintaining the same temperature

Sources & evidence

ORD record
ord-99abf33c5b954cc6b9cb7a709b6c79fc
Source dataset
uspto-grants-2016_03
Patent number
US09290446B2

Reaction notes

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