Dimethyl Sulfoxide → 1147531-61-0

HRID 1474646Notes

Reaction equation

HRID 1474646 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2([CH2:21][OH:22])[CH2:20][CH2:19]2)=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl.O>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2([CH:21]=[O:22])[CH2:19][CH2:20]2)=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 20252945(1-(4-Bromophenyl)cyclopropyl)methanol

Product 1

HCID 212573861147531-61-0Yield 97.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of DMSO (2.18 mL, 30.7 mmol) in dry DCM (15.0 mL) under nitrogen atmosphere, was added oxalyl chloride (1.21 mL, 14.2 mmol) at −78° C. The reaction mixture was stirred at this temperature for 30 min followed by addition of solution of (1-(4-bromophenyl)cyclopropyl)methanol (2.7 g, 11.8 mmol), in DCM (15.0 mL). The reaction mixture was stirred at −78° C. for 45 min followed by addition of triethylamine (8.2 mL, 59.2 mmol) and further stirring at same temperature for 15 min and then at r.t. for 15 min. The reaction mixture was diluted with DCM (100 mL) and water (100 mL). The organic layer was separated, dried over Na2SO4 and concentrated in vacuo to afford title compound (2.6 g, 93%) as viscous oil which was used as such in the next step.

Workup

  1. stirringThe reaction mixture was stirred at −78° C. for 45 min
  2. stirringfurther stirring at same temperature for 15 min
  3. waitat r.t. for 15 min
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c2bdd1d53bc4b1cb756721af62acdaf
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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