Isopropanol → 5-Bromo-2-chloro-3-(4-isopropoxybenzyl)thiophene

HRID 1469177Notes

Reaction equation

HRID 1469177 reaction equation
[Br:1][C:2]1[S:6][C:5]([Cl:7])=[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:3]=1.[CH:16]1[CH:21]=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=C[CH:17]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.CC(O)C>C1COCC1>[Br:1][C:2]1[S:6][C:5]([Cl:7])=[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([CH3:21])[CH3:17])=[CH:11][CH:10]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 666909044-((5-Bromo-2-chlorothiophen-3-yl)methyl)phenol

Product 1

HCID 666933955-Bromo-2-chloro-3-(4-isopropoxybenzyl)thiopheneYield 80.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of phenol 4 (1 g, 3.29 mmol) and PPh3 (1.8 g, 6.58 mmol) in THF (25 mL) was added DIAD (1.3 mL, 6.58 mmol) at room temperature. The mixture was stirred at room temperature for 30 min. 2-Propanol (0.4 mL, 4.94 mmol) was added to the reaction mixture. The reaction mixture was stirred at room temperature for 20 hours. The mixture was extracted with EtOAc/H2O (50 mL/50 mL) and was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica column chromatography (Biotage) to provide the desired product 6 (913 mg, 80%).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 20 hours
  2. extractionThe mixture was extracted with EtOAc/H2O (50 mL/50 mL)
  3. dry with materialwas dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica column chromatography (Biotage)

Sources & evidence

ORD record
ord-baa0466d3f8545ebb407f28e06053e55
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

Loading…