1-Methoxyethanol → 1-(-4-Bromophenethyloxy)-2-methoxyethane

HRID 580971Notes

Reaction equation

HRID 580971 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7]Br)=[CH:4][CH:3]=1.[CH3:11][O:12][CH:13](O)[CH3:14].[Cl-].[Na+].[OH2:18]>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][O:18][CH2:14][CH2:13][O:12][CH3:11])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 30156371-MethoxyethanolHCID 110108254-Bromophenethyl bromideHCID 57417360Sodium chloride; water

Product 1

HCID 544917921-(-4-Bromophenethyloxy)-2-methoxyethane

Procedure

4-bromophenethyl bromide (4.0 g) was added in a dropwise manner to a cooled solution of methoxyethanol (50 ml) and mercury II perchlorate (prepared from 3.39 g of mercury II oxide and 4.71 g of 60% perchloric acid). The mixture was stirred overnight at ambient temperature. Saturated brine (80 ml) was added, the mercury salts removed by filtration and washed with ether. The filtrate was extracted with ether (3×100 ml). The ether extracts were combined, washed with water (20 ml), saturated brine (20 ml), dried (MgSO4) and evaporated. The residue was purified by flash chromatography on silica gel using 10% ethyl acetate in toluene as eluent to give 1-(-4-bromophenethyloxy)-2-methoxyethane (2.2 g) as a colourless oil; NMR(CDCl3): 2.8-2.9(2H,t), 3.4(3H,s), 3.5-3.6(4H,m), 3.6-3.75(2H,t 7.05-7.15(2H,d) and 7.35-7.45(2H,d).

Workup

  1. customthe mercury salts removed by filtration
  2. washwashed with ether
  3. extractionThe filtrate was extracted with ether (3×100 ml)
  4. washwashed with water (20 ml), saturated brine (20 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by flash chromatography on silica gel using 10% ethyl acetate in toluene as eluent

Sources & evidence

ORD record
ord-733498324b964a4ca206f6bfeb47655c
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

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