Benzyl Bromide → 1-(Benzyloxy)-2-bromo-4-chlorobenzene

HRID 1276337Notes

Reaction equation

HRID 1276337 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Br:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[OH:23]>CN(C=O)C.O>[Br:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[O:23][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 696702-Bromo-4-chlorophenol

Product 1

HCID 115511251-(Benzyloxy)-2-bromo-4-chlorobenzeneYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

18.2 g (0.13 mol.) of potassium carbonate and 18.74 g (13.03 ml, 0.11 mol.) benzyl bromide is added to 2-bromo-4-chlorophenol (1) (25 g, 0. 12mol) in DMF (25 ml) under nitrogen. The reaction mixture is heated (oil bath temperature 115° C.) for 1.5 hours and then allowed to cool and left to stand overnight at RT. The reaction mixture is diluted with distilled water (100 ml) and then extracted with Et2O (2×100 ml). The organic extracts are combined, washed with 1M sodium hydroxide (100 ml) and concentrated in vacuo to leave a colorless oil. This oil is purified by flash chromatography (SiO2, pentane) to yield a colorless oil which crystallised on standing to give the title compound as a colorless solid, (29.14 g, 81%), m.p. 49-50.5° C. δH (250 MHz, CDCl3), 7.55 (d, J=2.6 Hz, 1H), 7.46 (m, 5H), 7.19 (dd, J=8.9, 2.5 Hz, 1H), 6.84 (d, J=8.8 Hz, 1H), 5.13 (s, 2H).

Workup

  1. temperatureto cool
  2. waitleft
  3. extractionextracted with Et2O (2×100 ml)
  4. washwashed with 1M sodium hydroxide (100 ml)
  5. concentrationconcentrated in vacuo
  6. customto leave a colorless oil
  7. customThis oil is purified by flash chromatography (SiO2, pentane)
  8. customto yield a colorless oil which
  9. customcrystallised

Sources & evidence

ORD record
ord-5b56f80b454d4255bdec0ca7a07eac4c
Source dataset
uspto-grants-2000_12
Patent number
US06166041

Reaction notes

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