Water → HCID 18800598, compound

HRID 1637700Notes

Reaction equation

HRID 1637700 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[Na+].[Na+].O>CN(C=O)C>[Br-:1].[CH2:9]([O:8][C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 78084-BromophenolHCID 10340Sodium Carbonate

Product 1

HCID 18800598HCID 18800598, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-bromophenol (40 mmol), benzylbromide (40 mmol) and Na2CO3 in DMF (200 mL) was stirred at room temperature for 24 hours and was then poured into water. A solid was collected and was further recrystallized from hexane to give 4-benzyloxybenzene bromide in almost quantitative yield. A solution of the bromide in THF (100 mL) was treated with BuLi (44 mmol) at -78° C. over 30 minutes and then with a solution of ZnI2 (40 mmol) in THF (40 mL) over 20 minutes. After the resulting mixture was warmed to room temperature over an hour, it was cooled to -78° C. and a solution of copper (I) cyanide (40 mmol) and lithium chloride (80 mmol) in THF (50 mL) was slowly added. The resulting mixture was warmed and stirred at -20° C. for 20 minutes, cooled to -78° C., and to it was added ethyl 2-(bromomethyl)acrylate (40 mmol). The resulting mixture was stirred at -78° C. for 2 hours and was then warmed to room temperature overnight. Ether and aqueous saturated ammonium chloride were added and filtered. The filtrate was washed with water and brine, and dried over MgSO4. Concentration gave a residue, which was purified by column chromatography with gradient solvent system (CH2Cl2 -EtOAc) to give the title compound (3.6 g, 30.4%): 1H NMP (CDCl3) δ7.44-7.26 (m, 5H),7.12 (d, J=8.4 Hz, 2H), 6.91 (d, J=8.4 Hz, 2H), 6.20 (s, 1H), 5.92 (s, 1H), 5.07 (s, 2H), 4.18 (q, J=7.4 Hz, 2H), 3.57 (s, 2H), 1.27 (t, J=7.4 Hz, 3H); MS: 314 (M+NH4)+.

Workup

  1. customA solid was collected
  2. customwas further recrystallized from hexane

Sources & evidence

ORD record
ord-9bfeada36b0f4ff48f103f943a1d7b4a
Source dataset
uspto-grants-2000_03
Patent number
US06043257

Reaction notes

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