Benzeneacetic acid, 4-bromo- → 1-(4-Bromophenyl)cyclohexane-1-carboxylic acid

HRID 2375222Notes

Reaction equation

HRID 2375222 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.Br[C:13]1[CH:18]=[CH:17]C(CC(OC2CCCCO2)=O)=[CH:15][CH:14]=1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:9]([OH:11])=[O:10])[CH2:17][CH2:18][CH2:13][CH2:14][CH2:15]2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 74654Benzeneacetic acid, 4-bromo-HCID 69202195HCID 69202195, compound

Product 1

HCID 167695091-(4-Bromophenyl)cyclohexane-1-carboxylic acidYield 25%

Procedure

The title compound was obtained in a manner analogous to that for 1-Phenylcyclohexanecarboxylic acid (1/3) starting with (4-bromophenyl)acetic acid (4d), via tetrahydro-2H-pyran-2-yl 2-(4-bromophenyl)acetate (5d). The crude product 1/9 was chromatographed on silica gel with petroleum ether-dioxane-acetic acid (85:15:2) and petroleum ether-tert-butylmethyl ether-acetic acid (8:2:0.1) as eluents to give 1-(4-bromophenyl)cyclohexanecarboxylic acid (1/9) in 25% yield. 1H NMR (CDCl3, HMDSO) δ: 1.17-1.92 (8H, m); 2.28-2.59 (2H, m); 7.33 (2H, d, J=8.8 Hz); 7.47 (2H, d, J=8.8 Hz); 10.34 (1H, br s).

Workup

  1. customThe crude product 1/9 was chromatographed on silica gel with petroleum ether-dioxane-acetic acid (85:15:2) and petroleum ether-tert-butylmethyl ether-acetic acid (8:2:0.1) as eluents

Sources & evidence

ORD record
ord-108a01a27cf54c49903b55452f2d8e3a
Source dataset
uspto-grants-2008_12
Patent number
US07465719B2

Reaction notes

Loading…