Benzyl Bromide → 1,1'-[(4-Bromo-1,3-phenylene)bis(oxymethylene)]dibenzene
Reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:14]=[CH:13][C:11](O)=[CH:10][C:9]=1[OH:15].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC(C)=O>[CH2:16]([O:15][C:9]1[CH:10]=[C:11]([O:4][CH2:1][C:8]2[CH:14]=[CH:13][CH:11]=[CH:10][CH:9]=2)[CH:13]=[CH:14][C:8]=1[Br:7])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 7.5 °C
Procedure
106.6 g (0.771 mol, 3 eq) of potassium carbonate (325 mesh) are added to a solution of 50.1 g (0.257 mol, 1 eq) of 4-bromoresorcinol at 97% in 500 ml of acetone. The reaction medium is cooled to 5-10° C. and 75 ml (0.630 mol, 2.45 eq) of benzyl bromide are added dropwise. The reaction medium is stirred at ambient temperature overnight and is then heated at 50° C. for 2 hours. The solvent is evaporated off and the residue is then taken up with a water/ethyl acetate mixture. The aqueous phase is extracted with ethyl acetate, and the organic phases are combined, washed with a saturated solution of sodium chloride, dried over magnesium sulphate, filtered and evaporated. The residue (114.34 g) is chromatographed on silica gel (600 g), elution being carried out with 90/10 heptane/dichloromethane. 94.4 g of 2,4-bis(benzyloxy)-1-bromobenzene are obtained in the form of white crystals. Yield=99%.
Workup
- temperatureis then heated at 50° C. for 2 hours
- customThe solvent is evaporated off
- extractionThe aqueous phase is extracted with ethyl acetate
- washwashed with a saturated solution of sodium chloride
- dry with materialdried over magnesium sulphate
- filtrationfiltered
- customevaporated
- customThe residue (114.34 g) is chromatographed on silica gel (600 g), elution
Sources & evidence
- ORD record
- ord-3efde474aba34262b8382b1896713753
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08697726B2
Reaction notes
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