Dimethylformamide → 5-(4-Bromobutoxy)-4-propyl-1,1-bis(trifluoromethyl)-1,3-dihydroisobenzofuran

HRID 552452Notes

Reaction equation

HRID 552452 reaction equation
CN(C)C=O.[CH2:6]([C:9]1[C:17]([OH:18])=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][O:12][C:13]2([C:23]([F:26])([F:25])[F:24])[C:19]([F:22])([F:21])[F:20])[CH2:7][CH3:8].[Br:27][CH2:28][CH2:29][CH2:30][CH2:31]Br.C(=O)([O-])[O-].[K+].[K+]>O>[Br:27][CH2:28][CH2:29][CH2:30][CH2:31][O:18][C:17]1[C:9]([CH2:6][CH2:7][CH3:8])=[C:10]2[C:14](=[CH:15][CH:16]=1)[C:13]([C:23]([F:26])([F:24])[F:25])([C:19]([F:20])([F:21])[F:22])[O:12][CH2:11]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 579008164-Propyl-1,1-bis(trifluoromethyl)-1,3-dihydroisobenzofuran-5-ol

Product 1

HCID 579007815-(4-Bromobutoxy)-4-propyl-1,1-bis(trifluoromethyl)-1,3-dihydroisobenzofuranYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A N,N-Dimethylformamide (10 mL) solution of 4-propyl-1,1-bis(trifluoromethyl)-1,3-dihydroisobenzofuran-5-ol (800 mg, 2.55 mol), 1,4-dibromobutane (2.75 mL, 12.73 mmol) and potassium carbonate (528 mg, 3.82 mmol) was stirred at room temperature overnight. The reaction solution was added with water and extracted with ethyl acetate. Subsequently, the organic layer was washed with saturated saline, dried using anhydrous sodium sulfate, and concentrated in vacuum. The obtained residue was purified by silica-gel column chromatography (hexane:ethyl acetate=50:1) and the title compound (1.136 g, 99%) was obtained as colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washSubsequently, the organic layer was washed with saturated saline
  3. customdried
  4. concentrationconcentrated in vacuum
  5. customThe obtained residue was purified by silica-gel column chromatography (hexane:ethyl acetate=50:1)

Sources & evidence

ORD record
ord-7b3af3f32a94410e963abafdad80b924
Source dataset
uspto-grants-2011_05
Patent number
US07951822B2

Reaction notes

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