Methyl iodide → HCID 21877302, compound

HRID 1816822Notes

Reaction equation

HRID 1816822 reaction equation
[Br:1]C1C=CC(O)=CC=1CCO.Br[CH:13]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][CH2:29][O:30][CH3:31])[CH:23]=1)[O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18].BrC1C=CC(OCOCC[Si](C)(C)C)=CC=1CCO.[OH-].[K+].IC>CS(C)=O.O>[Br:1][C:25]1[CH:26]=[CH:27][C:22]([O:21][CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])=[CH:23][C:24]=1[CH2:28][CH2:29][O:30][CH3:31]

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 21877429HCID 21877429, compoundHCID 21877550HCID 21877550, compoundHCID 86759688HCID 86759688, compound

Product 1

HCID 21877302HCID 21877302, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Preparation of 2-[2-Bromo-5-(2-trimethylsilanyl-ethoxymethoxy)-phenyl] was prepared in 65% yield by the substitution of 4-bromo-3-(2-hydroxy-ethyl)-phenol in the procedure described in Example 24(a), step (vi). 1H NMR (300 MHz, CDCl3) δ 7.43 (d, 1H, J=8.7 Hz), 6.97 (d, 1H, J=3.0 Hz), 6.82 (dd, 1H, J=8.7, 3.0 Hz), 5.19 (s, 2H), 3.88 (q, 2H, J=6.6 Hz), 3.74 (t, 2H, J=8.4 Hz), 2.99 (t, 2H, J=6.6 Hz), 1.42 (t, 1H, J=6.6 Hz), 0.94 (t, 2H, 1=8.4 Hz), −0.01 (s, 9H). {(2-[Bromo-3-(2-methoxy-ethyl)phenoxymethoxy]-ethyl}-trimethyl-silane: 2-[2-Bromo-5-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-ethanol (1.9 g, 6.0 mmol) was added to a solution of potassium hydroxide (1.35 g, 24 mmol) in DMSO (16 mL). Iodomethane (1.12 mL, 18 mmol) was added, and the solution stirred for 16 h. The reaction was diluted with water (50 mL) and extracted with ether (2×40 mL). Organics were washed with brine (40 mL), dried (Na2SO4) and concentrated in vacuo. Purification by silica gel chromatography (10% ether/hexanes) gave 1.28 g of (2-[4-bromo-3-(2-methoxy-ethyl)-phenoxymethoxy]-ethyl)-trimethyl-silane as a clear oil. 1H NMR (300 MHz, CDCl3) δ 7.40 (d, 1H, J=8.7 Hz), 6.96 (d, 1H, J=3.0 Hz), 6.80 (dd, 1H, J=8.7, 3.0 Hz), 5.18 (s, 2H), 3.74 (t, 2H, J=8.4 Hz), 3.60 (t, 2H, J=7.2 Hz), 3.37 (s, 3H), 2.98 (t, 2H, J=7.2 Hz), 0.95 (t, 2H, J=8.4 Hz), −0.01 (s, 9H).

Workup

  1. customPreparation of 2-[2-Bromo-5-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]
  2. extractionextracted with ether (2×40 mL)
  3. washOrganics were washed with brine (40 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography (10% ether/hexanes)

Sources & evidence

ORD record
ord-f1eacef3ec064289a5a313a3cef8c137
Source dataset
uspto-grants-2005_04
Patent number
US06884890B2

Reaction notes

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