Dimethylformamide → 1,1'-[(4-Bromo-1,3-phenylene)bis(oxymethylene)]dibenzene

HRID 1074498Notes

Reaction equation

HRID 1074498 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][C:3]=1O.[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:18](=[O:21])([O-])[O-].[K+].[K+].CN(C)C=O>CCOCC.CCCCC>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([O:6][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][C:3]=1[O:21][CH2:18][C:2]1[CH:8]=[CH:7][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 811054-Bromoresorcinol

Product 1

HCID 128821681,1'-[(4-Bromo-1,3-phenylene)bis(oxymethylene)]dibenzeneYield 30%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8003PentaneSolvent

Procedure

A mixture of 75.0 g. (0.397 mol.) of 4-bromoresorcinol, 95.1 ml. (0.80 mol.) of benzylbromide and 331 g. (2.4 mol.) of anhydrous potassium carbonate in 400 ml. of N,N-dimethylformamide was stirred for 12 hours at 25° C. and for 4 hours at 85° C. The reaction mixture was cooled and added to one liter of ice--200 ml. pentane--100 ml. ether. The organic phase was washed with three 500 ml. portions of water, dried over magnesium sulfate and evaporated to an oil. The oil was rapidly chromatographed on 400 g. of silica gel eluted with 20% ether-pentane to yield 80 g. of oil. The chromatographed oil was crystallized from pentane at 0° C. to yield 45.0 g. (30%) of the title compound, M.P. 37°-38° C.

Workup

  1. additionA mixture of 75.0 g
  2. temperatureThe reaction mixture was cooled
  3. washThe organic phase was washed with three 500 ml
  4. dry with materialportions of water, dried over magnesium sulfate
  5. customevaporated to an oil
  6. customThe oil was rapidly chromatographed on 400 g
  7. washof silica gel eluted with 20% ether-pentane
  8. customto yield 80 g
  9. customThe chromatographed oil was crystallized from pentane at 0° C.
  10. customto yield 45.0 g

Sources & evidence

ORD record
ord-deb725b4e00f43f09f5624598d44cff6
Source dataset
uspto-grants-1983_07
Patent number
US04391827

Reaction notes

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