Dimethyl Sulfoxide → HCID 66777025, compound

HRID 2091194Notes

Reaction equation

HRID 2091194 reaction equation
CS(C)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Br:18][C:19]1[C:23]2[CH:24]=[C:25]([O:28][CH3:29])[CH:26]=[CH:27][C:22]=2[O:21][C:20]=1[CH:30]([CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)[OH:31].C(N(CC)CC)C>O1CCCC1>[Br:18][C:19]1[C:23]2[CH:24]=[C:25]([O:28][CH3:29])[CH:26]=[CH:27][C:22]=2[O:21][C:20]=1[C:30]([CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)=[O:31]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 66777987HCID 66777987, compound

Product 1

HCID 66777025HCID 66777025, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of dimethyl sulfoxide (831 mL) and tetrahydrofuran (20 mL) was added trifluoroacetic acid anhydride (1.63 mL) at −78° C., and the mixture was stirred for 30 min, and a solution (20 mL) of (3-bromo-5-methoxy-1-benzofuran-2-yl)(cyclohexyl)methanol (2.03 g) synthesized in Example A102(4) in tetrahydrofuran was added. The reaction mixture was stirred under argon atmosphere at −78° C. for 1 hr, triethylamine (3.33 mL) was added, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (15% ethyl acetate/hexane) to give the title object compound (1.52 g, 75%) as a white solid.

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred under argon atmosphere at −78° C. for 1 hr
  3. stirringthe mixture was stirred at room temperature for 1 hr
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2b3f3a6d4e014213819877382c112c76
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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