(+/-)-4-(4-Bromophenyl)-2-methyl-2-(methylsulfonyl)butanoic acid → HCID 66577888, compound

HRID 533577Notes

Reaction equation

HRID 533577 reaction equation
[CH3:1][C:2]([S:24]([CH3:27])(=[O:26])=[O:25])([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][CH:11]=1)[C:3]([O:5]CC)=[O:4].BrC1C=CC(CCC(C)(S(C)(=O)=O)C(O)=O)=CC=1>>[CH3:1][C:2]([S:24]([CH3:27])(=[O:25])=[O:26])([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][CH:11]=1)[C:3]([OH:5])=[O:4]

Participants

3

Reactant 2

HCID 66577906(+/-)-4-(4-Bromophenyl)-2-methyl-2-(methylsulfonyl)butanoic acidHCID 66577975HCID 66577975, compound

Product 1

HCID 66577888HCID 66577888, compoundYield 24.3%

Procedure

The title compound (247 mg, 24%) was prepared from ethyl 2-methyl-2-(methylsulfonyl)-4-[4-(phenoxymethyl)phenyl]butanoate (1.1 g, 2.8 mmol) following the general procedure of step 3, from Preparation 2, for the formation of compound (II). MS (LC/MS) m/z 361.2 (M−1). 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.62-1.69 (m, 3H) 2.06-2.18 (m, 1H) 2.42-2.65 (m, 2H) 2.74-2.86 (m, 1H) 3.10 (s, 3H) 5.04 (s, 2H) 6.91 (t, J=7.42 Hz, 1H) 6.97 (d, J=7.81 Hz, 2H) 7.22-7.29 (m, 4H) 7.37 (d, J=8.20 Hz, 2H).

Workup

  1. customfrom Preparation 2

Sources & evidence

ORD record
ord-c5eb7ff6a09a43c69408caef7539c2f8
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

Loading…