Hydrochloric Acid → Methyl cis-2-(4-bromobenzoyl)cyclohexanecarboxylate

HRID 30853

Reaction equation

HRID 30853 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C@H:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]2[C:14]([OH:16])=[O:15])=[O:7])=[CH:4][CH:3]=1.[CH3:19]OC(OC)(C)C.Cl>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C@H:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]2[C:14]([O:16][CH3:19])=[O:15])=[O:7])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 64952,2-DimethoxypropaneHCID 2725094cis-2-(4-Bromobenzoyl)cyclohexanecarboxylic acid

Product 1

HCID 67147291Methyl cis-2-(4-bromobenzoyl)cyclohexanecarboxylateYield 42.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of cis-2-(4-bromobenzoyl)-1-cyclohexanecarboxylic acid (4.0 g, 12.85 mmol) in MeOH (50 mL) was added 2,2-dimethoxypropane (2.01 g, 19.28 mmol) and HCl (4.0 M in dioxane, 1.20 mL). The resulting solution was stirred at 40° C. for 3 days, and then evaporated to dryness. The resulting residue was purified by flash chromatography (Biotage Flash 40M) using 3 to 6% ethyl acetate in hexanes to afford methyl cis-2-(4-bromobenzoyl)cyclohexane-carboxylate (1.76 g, 42%). LC-MS ret. time 3.40; m/z 326 (MH+); 1H NMR (400 MHz, CD2Cl2) δ 1.35-1.51 (m, 3H), 1.72-1.86 (m, 2H), 1.91-2.05 (m, 2H), 2.11-2.20 (m, 1H), 2.74 (m, 1H), 3.58 (s, 3H), 3.82 (q, 1H), 7.62 (m, 2H), 7.73 (m, 2H).

Workup

  1. customevaporated to dryness
  2. customThe resulting residue was purified by flash chromatography (Biotage Flash 40M)

Sources & evidence

ORD record
ord-ed2ca1ed2ce048fc944a80d3d52954ff
Source dataset
uspto-grants-2008_09
Patent number
US07423156B2

Linked notes

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