Water → HCID 22731282, compound

HRID 2085577Notes

Reaction equation

HRID 2085577 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1.Cl[CH:14]([O:16]C(Cl)Cl)Cl.O>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[O:16])[C:5]2[O:9][CH2:8][C:7]([CH3:10])([CH3:11])[C:6]=2[CH:12]=1

Participants

6

Reactant 3

HCID 962WaterHCID 558102Bis(dichloromethyl) etherHCID 53235955-Bromo-3,3-dimethyl-2,3-dihydro-1-benzofuran2×

Product 1

HCID 22731282HCID 22731282, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred, cooled (ice-bath) solution of 5-bromo-3,3-dimethyl-2,3-dihydrobenzofuran (Intermediate 2, 0.4 g, 1.57 mmol) in anhydrous dichloromethane(4 mL), titanium tetrachloride (0.172 mL, 1.57 mmol) was added followed by dichloromethyl ether (0.14 mL, 1.57 mmol). The reaction mixture was allowed to warm to room temperature and at the end of 3 hr, the reaction mixture was poured into iced water and extracted with diethyl ether. The organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated to a residue that on flash column chromatography using 2.5% ethyl acetate in hexane as the eluent afforded the title compound (0.25 g, 63%).

Workup

  1. additionwas added
  2. extractionextracted with diethyl ether
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated to a residue that on flash column chromatography

Sources & evidence

ORD record
ord-65f55275dbab412a88bdae2e5d49c9df
Source dataset
uspto-grants-2004_04
Patent number
US06720423B2

Reaction notes

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