4-Bromophenol → 1-Bromo-4-(2-methoxyethoxy)benzene

HRID 2240273Notes

Reaction equation

HRID 2240273 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9][O:10][CH2:11][CH2:12]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:12][CH2:11][O:10][CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 78084-BromophenolHCID 80192-MethoxyethanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylate

Product 1

HCID 140261831-Bromo-4-(2-methoxyethoxy)benzeneYield 83.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

4-Bromophenol (8.65 g; 0.05 mol), 2-methoxyethanol (1.1 eq.; 0.055 mol; 4.36 ml) and triphenylphosphine (1.1 eq.; 0.055 mol; 14.4 g) are dissolved in 210 ml of toluene. The reaction medium is brought to 54° C. and diisopropyl azodicarboxylate (1.0 eq.; 0.05 mol; 10.1 g) dissolved in 21 ml of toluene is added dropwise. The reaction medium is left at 54° C. for one hour and then overnight at room temperature, and is then evaporated to dryness. The crude product is purified by flash chromatography on silica on a gradient of heptane comprising 0-100% DCM to give 9.6 g of the expected product in the form of an oil.

Workup

  1. customis brought to 54° C.
  2. additionis added dropwise
  3. customovernight at room temperature, and is then evaporated to dryness
  4. customThe crude product is purified by flash chromatography on silica on a gradient of heptane comprising 0-100% DCM

Sources & evidence

ORD record
ord-b12234da81dd4536ba041be15cd150d3
Source dataset
uspto-grants-2010_05
Patent number
US07723358B2

Reaction notes

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