Methyl iodide → 4-Bromo-2-(methoxymethyl)thiophene

HRID 456528Notes

Reaction equation

HRID 456528 reaction equation
[H-].[Na+].[CH3:3]I.[Br:5][C:6]1[CH:7]=[C:8]([CH2:11][OH:12])[S:9][CH:10]=1>O1CCCC1>[Br:5][C:6]1[CH:7]=[C:8]([CH2:11][O:12][CH3:3])[S:9][CH:10]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2795484(4-Bromo-2-thienyl)methanol

Product 1

HCID 150183124-Bromo-2-(methoxymethyl)thiophene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add sodium hydride (737 mg, 29.23 mmol, 1.10 equivalents, 95%) to a solution containing methyl iodide (1.65 mL, 26.57 mmol, 1.00 equivalents) and (4-bromo-thiophen-2-yl)-methanol (5.13 g, 26.57 mmol, 1.00 equivalents) in tetrahydrofuran (dry, 25 mL). Stir the resulting mixture at room temperature overnight and evaporate. Partition the residue between water (100 mL) and dichloromethane (100 mL). Extract the aqueous layer with dichloromethane (100 mL), combine the organic layers, dry over magnesium sulfate, filter and evaporate to yield the desired product as a yellow oil.

Workup

  1. customevaporate
  2. customPartition the residue between water (100 mL) and dichloromethane (100 mL)
  3. extractionExtract the aqueous layer with dichloromethane (100 mL)
  4. dry with materialdry over magnesium sulfate
  5. filtrationfilter
  6. customevaporate

Sources & evidence

ORD record
ord-ac324890fddb41bea7ead4ba5dc52f23
Source dataset
uspto-grants-2007_03
Patent number
US07186724B2

Reaction notes

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