Benzyl Chloride → 1-Bromo-4-phenylmethoxybenzene

HRID 650727Notes

Reaction equation

HRID 650727 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CC(C)=O.[Na+].[I-]>[CH2:15]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 78084-BromophenolHCID 11430Potassium Carbonate

Product 1

HCID 1388351-Bromo-4-phenylmethoxybenzeneYield 75.4%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 180AcetoneSolvent

Procedure

200 g (1.16 mol) of 4-bromophenol was dissolved in 2.1 L acetone under argon. Then 320 g (2.31 mol) K2CO3 and 3.465 g (23.1 mmol) NaI were added. The mixture was stirred at room temperature and 292.7 g (2.31 mol) of benzyl chloride was added during 1 h. Then the mixture was boiled during 48 h. The acetone (ca. 500 mL) was partially removed on the rotary evaporator. 1.2 L 10% aq. Na2CO3 was added to the residue. After extraction with ethyl acetate (1×1 L+2×500 mL) the organic phase was washed with 1 L of a half-saturated NaCl solution. After drying over Na2SO4 and concentrating, the main part of the benzyl chloride was removed. 400 mL of pentane was added to the residue. The crystallisation began during stirring at 0° C. The crystals were separated and washed with 2×150 mL pentane and dried during 2 h at 15 mbar (40 C° bath temperature) and 2 h under high vacuum at room temperature to yield 230 g (75%) 4-benzyloxybromobenzene.

Workup

  1. customThe acetone (ca. 500 mL) was partially removed on the rotary evaporator
  2. addition1.2 L 10% aq. Na2CO3 was added to the residue
  3. extractionAfter extraction with ethyl acetate (1×1 L+2×500 mL) the organic phase
  4. washwas washed with 1 L of a half-saturated NaCl solution
  5. dry with materialAfter drying over Na2SO4
  6. concentrationconcentrating
  7. customthe main part of the benzyl chloride was removed
  8. addition400 mL of pentane was added to the residue
  9. customThe crystallisation
  10. stirringduring stirring at 0° C
  11. customThe crystals were separated
  12. washwashed with 2×150 mL pentane
  13. customdried during 2 h at 15 mbar (40 C° bath temperature) and 2 h under high vacuum at room temperature

Sources & evidence

ORD record
ord-11f8a3029ec445e2bd5ce3bec92f8342
Source dataset
uspto-grants-2001_08
Patent number
US06274735B1

Reaction notes

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