Toluene → HCID 67958383, compound

HRID 2278332Notes

Reaction equation

HRID 2278332 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][C:13]([CH3:15])=[CH2:14])[C:6]=1Br)(=[O:3])[CH3:2].C1(C)C=CC=CC=1.C([SnH](CCCC)CCCC)CCC>>[C:1]([O:4][C:5]1[C:6]2[C:13]([CH3:15])([CH3:14])[CH2:12][O:11][C:7]=2[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 1140TolueneHCID 5948TributylstannaneHCID 67958681HCID 67958681, compound2×

Product 1

HCID 67958383HCID 67958383, compoundYield 76.7%

Conditions

Temperature
100 °C

Procedure

To a solution of 2-bromo-3-[(2-methyl-2-propen-1-yl)oxy]phenyl acetate (Intermediate 39, 2.324 g) in toluene (20 ml) AIBN (1.606 g, 9.78 mmol) and tributylstannane (4.73 g, 16.30 mmol) were added. The reaction mixture was stirred and heated at 100° C. for 2 hours, then was left at room temperature for 4 hours. The reaction was quenched with water (60 ml) and extracted with ethyl acetate (3 times 50 ml). The combined organic layers were dried over sodium sulphate, filtered and evaporated. The residue was purified by flash chromatography on silica gel using a 100 g-SNAP column and cyclohexane/ethyl acetate from 100/0 to 70/30 as eluent to afford the title compound as a colourless oil (1.290 g).

Workup

  1. customThe reaction was quenched with water (60 ml)
  2. extractionextracted with ethyl acetate (3 times 50 ml)
  3. dry with materialThe combined organic layers were dried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel using a 100 g-SNAP column and cyclohexane/ethyl acetate from 100/0 to 70/30 as eluent

Sources & evidence

ORD record
ord-e71add6c8df0411a9228ade506b1bf00
Source dataset
uspto-grants-2015_09
Patent number
US09133175B2

Reaction notes

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