2-Bromoanisole → HCID 11558102, compound

HRID 2270482Notes

Reaction equation

HRID 2270482 reaction equation
[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14].[CH3:15][Sn:16](Cl)([CH3:18])[CH3:17]>C(OCC)C>[CH3:15][Sn:16]([CH3:18])([CH3:17])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14]

Participants

5

Reactant 3

HCID 113582-BromoanisoleHCID 14016Trimethyltin chlorideHCID 178418339Butyllithium

Product 1

HCID 11558102HCID 11558102, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a stirring solution of n-BuLi (2.6 mL, 2.5M in hexane, 6.42 mmol) in diethyl ether (2.5 mL) at −78° C. was added 2-bromoanisole (1.0 g, 5.35 mmol) in diethyl ether (2 mL) dropwise. After stirring for 1 h at −78° C., trimethyltin chloride (6mL, 1.0M in THF, 6.42 mmol) was added dropwise. The mixture was allowed to stir an additional 2 h while slowly warming to room temperature. The mixture was then washed with saturated aqueous NaHCO3. The aqueous layer was extracted with diethyl ether (1×5 mL) and the organic layers were combined, dried (MgSO4), filtered and concentrate. The residue was purified by column chromatography (silica gel, hexane) to yield the title compound as a colorless oil (1.11 g, 76%). 1HNMR (400 MHz, CDCl3)δ7.47 (d, 1H), 7.40 (t, 1H), 7.05 (t, 1H), 6.90 (d, 1H), 3.36 (s, 3H), 0.34 (s, 9H).

Workup

  1. stirringto stir an additional 2 h
  2. temperaturewhile slowly warming to room temperature
  3. washThe mixture was then washed with saturated aqueous NaHCO3
  4. extractionThe aqueous layer was extracted with diethyl ether (1×5 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrate
  8. customThe residue was purified by column chromatography (silica gel, hexane)

Sources & evidence

ORD record
ord-10786cb3f18645b8a60283cedb1bc4d0
Source dataset
uspto-grants-2001_12
Patent number
US06331542B1

Reaction notes

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