Benzene, 1-iodo-3-methoxy- → 1-(Bromomethyl)-2-iodo-4-methoxybenzene

HRID 1188751Notes

Reaction equation

HRID 1188751 reaction equation
CO[CH2:3][Br:4].[I:5][C:6]1[CH:7]=[C:8]([O:12][CH3:13])[CH:9]=[CH:10][CH:11]=1.IC1C=C(O)C=CC=1C[C@@H](C(O)=O)N>C(O)(=O)C.O>[Br:4][CH2:3][C:11]1[CH:10]=[CH:9][C:8]([O:12][CH3:13])=[CH:7][C:6]=1[I:5]

Participants

6

Reactant 3

HCID 69839Benzene, 1-iodo-3-methoxy-HCID 83093Bromomethyl methyl etherHCID 1354612-Iodotyrosine

Product 1

HCID 112096011-(Bromomethyl)-2-iodo-4-methoxybenzeneYield 45%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Bromomethyl methyl ether (5.14 ml, 63.2 mmol) was added to a solution of 3-iodoanisole 19 (7.4 g, 31.6 mmol) in glacial acetic acid (17.0 mL) and the colorless solution was stirred for 2 days at room temperature as set forth in T. J. McCord, D. E. Thornton, K. L. Hulme and A. L. Davis, “Synthesis and Microbiological Properties of 2-Iodotyrosine and Related Compounds.” Texas J. Sci., 30, pp 357-363 (1978). The reaction mixture was diluted with water and then extracted with ethyl acetate. The organic phase was dried over Na2SO4, filtered and evaporated to produce a yellow oil which was purified by silica gel column chromatography to yield 1-bromomethyl-2-iodo-4-methoxybenzene (20) as a white solid (4.59 g, 45%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customto produce a yellow oil which
  6. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-16b1d741e30c4908aedc3fc6a8afeedb
Source dataset
uspto-grants-2014_03
Patent number
US08674101B2

Reaction notes

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