2-Bromoanisole → HCID 11558102, compound

HRID 1977479Notes

Reaction equation

HRID 1977479 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×

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 −78C. was added 2-bromoanisole (1.0 g, 5.35 mmol) in diethyl ether (2mL) dropwise. After stirring for 1h at −78C., trimethyltin chloride (6.4 mL, 1.0M in THF, 6.42 mmol) was added dropwise. The mixture was allowed to stir an additional 2h while slowly warming to room temperature. The mixture was then washed with saturated aqueous NaHCO3. The aqueous layer was extracted with diethyl ether (1×50 mL) and the organic layers were combined, dried (MgSO4), filtered and concentrated. 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) δ 7.47 (d, 1H), 7.40 (t, 1H), 7.05 (t, 1H), 6.90 (d, 1H), 3.36 (s, 3H), 0.34 (s, 9H).

Workup

  1. washThe mixture was then washed with saturated aqueous NaHCO3
  2. extractionThe aqueous layer was extracted with diethyl ether (1×50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (silica gel, hexane)

Sources & evidence

ORD record
ord-fea5130960e14bd19cbfe4d2a01f554f
Source dataset
uspto-grants-2001_05
Patent number
US06232342B1

Reaction notes

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