Hydrogen Bromide → HCID 67513711, compound

HRID 1526432Notes

Reaction equation

HRID 1526432 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C:5]([CH3:18])([CH3:17])[CH2:6][CH2:7][CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[Cl:16])[CH3:2].[BrH:20]>C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:19])[C:5]([CH3:18])([CH3:17])[CH2:6][CH2:7][CH2:8][CH:9]([Br:20])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[Cl:16])[CH3:2]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 67512202HCID 67512202, compound

Product 1

HCID 67513711HCID 67513711, compoundYield 80.14%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6-(2-Chlorophenyl)-2,2-dimethylhex-5-enoic acid ethyl ester (15 g, 53.6 mmol) was dissolved in glacial acetic acid (150 mL). The solution was cooled in an ice-bath (ca. 15° C.) while dry hydrogen bromide was passed into the solution for 8 h. The reaction mixture was poured into ice-water (250 mL) and extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with saturated NaHCO3 solution (100 mL), dried over Na2SO4, and concentrated under reduced pressure. The crude product (18 g) was purified by column chromatography (silica gel, ethyl acetate/heptane=1/20 to 1/10) to provide 6-bromo-6-(2-chlorophenyl)-2,2-dimethylhexanoic acid ethyl ester (15.5 g, 80.14%) as a yellow oil. 1H NMR (Field: 300 MHz, Solvent: CDCl3/TMS) δ (ppm): 7.58 (d, 1H, J=7.8 Hz), 7.34 (t, 1H, J=7.8 Hz), 7.27 (d, 1H, J=7.2 Hz), 7.21 (t, 1H, J=7.2 Hz), 5.45 (t, 1H, J=8.1 Hz), 4.09 (q, 2H, J=6.9 Hz), 2.19 (m, 2H), 1.55 (m, 2H), 1.24 (t, 3H, J=6.9 Hz), 1.14 (s, 6H). 13C NMR (Field: 75 MHz, Solvent: CDCl3/TMS) δ (ppm): 177.45, 139.25, 132.64, 129.64, 129.27, 128.75, 127.43, 60.36, 49.97, 42.17, 39.84, 39.51, 25.41, 25.20, 23.67, 14.43. MS (GC-CI): Calculated for C16H22BrClO2 (MH)+: 361.0564. found 361.0547.

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. washThe combined organic extracts were washed with saturated NaHCO3 solution (100 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product (18 g) was purified by column chromatography (silica gel, ethyl acetate/heptane=1/20 to 1/10)

Sources & evidence

ORD record
ord-565e76f9c65543488418a26a20bb4739
Source dataset
uspto-grants-2015_07
Patent number
US09085585B2

Reaction notes

Loading…