3-Bromophenol → ((3-Bromophenoxy)methyl)cycloheptane

HRID 1523122Notes

Reaction equation

HRID 1523122 reaction equation
[CH:1]1([CH2:8][OH:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:10][C:11]1[CH:12]=[C:13](O)[CH:14]=[CH:15][CH:16]=1>>[Br:10][C:11]1[CH:16]=[C:15]([CH:14]=[CH:13][CH:12]=1)[O:9][CH2:8][CH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 115633-BromophenolHCID 78193Cycloheptanemethanol

Product 1

HCID 67317652((3-Bromophenoxy)methyl)cycloheptane

Procedure

Cycloheptylmethanol was coupled with 3-bromophenol following the method used in Example 10. After concentration under reduced pressure, hexanes was added. The mixture was stirred and sonicated then the precipitate was removed by filtration and the solids washed with hexanes. The combined filtrates were concentrated under reduced pressure. Purification by flash chromatography (10 to 50% EtOAc-hexanes gradient) gave ((3-bromophenoxy)methyl)cycloheptane. (Yield 1.0697 g, 56%): 1H NMR (400 MHz, CDCl3) δ 7.12 (t, J=8.4, 1H), 7.06-7.04 (m, 2H), 6.82 (dq, J=8.0, 1.2, 1H), 3.70 (d, J=6.4, 2H), 1.91-1.98 (m, 1H), 1.81-1.88 (m, 2H), 1.42-1.72 (m, 8H), 1.24-1.34 (m, 2H).

Workup

  1. concentrationAfter concentration under reduced pressure, hexanes
  2. additionwas added
  3. customsonicated
  4. customthe precipitate was removed by filtration
  5. washthe solids washed with hexanes
  6. concentrationThe combined filtrates were concentrated under reduced pressure
  7. customPurification by flash chromatography (10 to 50% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-2db4aedcc70f43bf92f48fe32ba9bcbf
Source dataset
uspto-grants-2015_07
Patent number
US09079825B2

Reaction notes

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