2-Bromophenol → 1-(Benzyloxy)-2-bromobenzene

HRID 1814350Notes

Reaction equation

HRID 1814350 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)([O-])[O-].[K+].[K+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 72442-BromophenolHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 5618281-(Benzyloxy)-2-bromobenzeneYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 42 g (242 mmol) 2-bromophenol, 100 g (726 mmol) potassium carbonate and 45.6 g (266.4 mmol) benzyl bromide in 500 mL absolute ethanol was heated to reflux for 18 h. The reaction mixture was cooled to 5° C. in an ice/water bath and filtered. The filtered solid was washed with 200 mL dichloromethane. The filtrate was concentrated and the residue purified over silica eluting with hexanes to give 54 g (205 mmol, 85%) of 1-bromo-2-benzyloxy-benzene as a colorless oil. 1H NMR (400 MHz) CDCl3 7.54-7.56 (d, 1H), 7.46-7.48 (d, 2H), 7.28-7.40 (m, 3H), 6.90-6.93 (d,1H), 6.81-6.85 (t, 1H), 5.14 (s, 2H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 h
  3. filtrationfiltered
  4. washThe filtered solid was washed with 200 mL dichloromethane
  5. concentrationThe filtrate was concentrated
  6. customthe residue purified over silica eluting with hexanes

Sources & evidence

ORD record
ord-178773c094f14c5f975a1989dcf82729
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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