Quinoline → 5-Bromo-3,3-dimethyl-2,3-dihydro-1-benzofuran

HRID 460283

Reaction equation

HRID 460283 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]C)=[C:4]([C:10]([CH3:14])([CH3:13])[CH2:11]Cl)[CH:3]=1.Cl.N1C=CC=CC=1.N1C2C(=CC=CC=2)C=CC=1>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[O:8][CH2:14][C:10]([CH3:11])([CH3:13])[C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 7047QuinolineHCID 46057784-Bromo-2-(2-chloro-1,1-dimethylethyl)anisoleHCID 10176127Pyridinium chloride

Product 1

HCID 53235955-Bromo-3,3-dimethyl-2,3-dihydro-1-benzofuranYield 98%

Procedure

A mixture of 4-bromo-2-(2-chloro-1,1-dimethyl-ethyl)-1-methoxy-benzene (65 g, 0.234 mol), pyridine hydrochloride (121.8 g, 1.054 mol) and quinoline (110.67 mL, 0.936 mol) was refluxed at 164° C.–167° C. under argon for 5 hrs. After cooling to room temperature the reaction mixture was treated with ice-cold 6N HCl and extracted twice with ether. The organic layers were combined, dried (MgSO4), filtered and evaporated. The residue was purified on silica gel (10% ethyl acetate in hexane) to give 52 g of 5-bromo-3,3-dimethyl-2,3-dihydro-benzofuran (98%). 1H NMR (300 MHz; CDCl3): δ 1.32 (s, 6H), 4.23 (s, 2H), 6.67 (d, J=8.1 Hz, 1H), 7.19 (m, 2H).

Workup

  1. temperaturewas refluxed at 164° C.–167° C. under argon for 5 hrs
  2. extractionextracted twice with ether
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified on silica gel (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-74232fb214504097af288aa320d9d3b5
Source dataset
uspto-grants-2007_03
Patent number
US07196108B2

Linked notes

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