Iodoethane → 2-Bromophenetole

HRID 870466

Reaction equation

HRID 870466 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].I[CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 72442-BromophenolHCID 11430Potassium Carbonate

Product 1

HCID 685002-BromophenetoleYield 95.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Into a 500-mL round-bottom flask was placed CH3COCH3 (200 mL), 2-bromophenol (10.38 g, 60.00 mmol, 1.00 equiv), iodoethane (28.08 g, 180.04 mmol, 3.00 equiv) and potassium carbonate (33.12 g, 239.64 mmol, 3.99 equiv). The resulting solution was heated to reflux overnight in an oil bath. The solids were filtered out. The filtrate was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:100). Purification afforded 11.48 g (95%) of 1-bromo-2-ethoxybenzene as a colorless oil.

Workup

  1. customInto a 500-mL round-bottom flask was placed
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux overnight in an oil bath
  4. filtrationThe solids were filtered out
  5. concentrationThe filtrate was concentrated under vacuum
  6. customPurification

Sources & evidence

ORD record
ord-c41bb86b516b4a38ad60daf8e2dc2224
Source dataset
uspto-grants-2015_03
Patent number
US08969557B2

Linked notes

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