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

HRID 1463924Notes

Reaction equation

HRID 1463924 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(#N)C>[CH2:15]([O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])[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 97.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Bromophenol (6.7 ml, 57.8 mmole) was dissolved in 200 ml acetonitrile in a 500 ml one neck round bottom flask under nitrogen. The solution was treated successively potassium carbonate (32 g, 231 mmole) and benzyl bromide (6.9 ml, 57.8 mmole). The reaction mixture was stirred for 6 hours at room temperature. The insoluble salts were removed by filtration and the filtrate was concentrated in vacuo to a pale oil. The oil was taken up in 100 ml diethyl ether and the mixture was washed successively with 2×25 ml 1N sodium hydroxide and 1×25 ml saturated sodium chloride. The organics were dried over magnesium sulfate and were concentrated in vacuo to give 14.8 g (97%) of 2-benzyloxy-bromobenzene as a pale oil.

Workup

  1. customThe insoluble salts were removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo to a pale oil
  3. washthe mixture was washed successively with 2×25 ml 1N sodium hydroxide and 1×25 ml saturated sodium chloride
  4. dry with materialThe organics were dried over magnesium sulfate
  5. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-5276f0de880d4e049ee81763b26c9f62
Source dataset
uspto-grants-1994_04
Patent number
US05302613

Reaction notes

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