Dichloromethane → 2-(1-Methylcyclohexyl)-4-bromoanisole

HRID 860568Notes

Reaction equation

HRID 860568 reaction equation
[CH3:1][C:2]1(O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.[CH2:17](Cl)Cl>OS(O)(=O)=O>[CH3:1][C:2]1([C:14]2[CH:15]=[C:10]([Br:9])[CH:11]=[CH:12][C:13]=2[O:16][CH3:17])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 78084-BromophenolHCID 115501-Methylcyclohexanol

Product 1

HCID 106843592-(1-Methylcyclohexyl)-4-bromoanisoleYield 13%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A mixture of 1-methylcyclohexanol (100.00 g, 0.876 mol) and 4-bromophenol (101.01 g, 0.584 mol) in CH2Cl2 (1.0 L) and H2SO4 (44 mL) was heated to reflux for 4 days. The mixture was cooled to RT. The reaction was poured in a separatory funnel and washed with water, 0.5 N NaHCO3 (till neutralized), brine and dried (MgSO4). The mixture was filtered, evaporated and the residue was purified on silica gel (eluant: hexane: CH2Cl2, 4:1) to give a total amount of 2-(1-methylcyclohexyl)-4-bromoanisole as an oil (29.70 g, 13%). 1H NMR (300 MHz, CDCl3): δ 1.30 (s, 3H), 1.30–1.70 (m, 8 H), 2.00–2.15 (m, 2H), 4.87 (s, 1H), 6.54 (d, J=8.4 Hz, 1H), 7.15 (dd, J1=8.4 Hz, J2=2.4 Hz, 1H), 7.36 (d, J=2.4 Hz, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 days
  3. additionThe reaction was poured in a separatory funnel
  4. washwashed with water, 0.5 N NaHCO3 (till neutralized), brine
  5. dry with materialdried (MgSO4)
  6. filtrationThe mixture was filtered
  7. customevaporated
  8. customthe residue was purified on silica gel (eluant: hexane: CH2Cl2, 4:1)

Sources & evidence

ORD record
ord-84d2133b76a14975a4f125ee41a8d61e
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

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