HCID 21100462, compound → HCID 10168177, compound

HRID 1352238Notes

Reaction equation

HRID 1352238 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:29][C:30]([OH:32])=[O:31])[CH:5]=[C:6]([Br:28])[C:7]=1[O:8][C:9]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[C:12]([OH:18])=[CH:11][C:10]=1[C:19](=[O:27])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[CH:21]=1>O=S(Cl)Cl.CO>[Br:1][C:2]1[CH:3]=[C:4]([CH2:29][C:30]([OH:32])=[O:31])[CH:5]=[C:6]([Br:28])[C:7]=1[O:8][C:9]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[C:12]([O:18][CH2:2][CH2:3][C:4]([CH3:29])=[CH2:5])=[CH:11][C:10]=1[C:19](=[O:27])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[CH:21]=1

Participants

4

Reactant 1

HCID 21100462HCID 21100462, compound

Product 1

HCID 10168177HCID 10168177, compoundYield 109.8%

Reagents, catalysts & solvents 2

HCID 24386Thionyl ChlorideCatalystHCID 887MethanolSolvent

Procedure

Five drops of SOCl2 was added to a solution of 3,5-dibromo-4-[4-hydroxy-5-isopropyl-2 -(3-methylbenzoyl)phenoxy]phenylacetic acid (0.30 g, 0.52 mmol), in 20 mL MeOH. The mixture was stirred at room temperature for 12 h and concentrated leaving the title compound (0.18 g, 60%). 1H NMR (CDCl3): δ 7.9–7.7 (m, 2H), 7.5–7.1 (m, 4H), 6.9 (s, 1H), 6.2 (s, 1H), 4.7 (s, 3H), 4.5 (s, 2H), 3.1 (m, 1H), 2.4 (s, 3H), 1.1 (d, 6H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-d7edf0c8b7d643c4829319d399866f37
Source dataset
uspto-grants-2007_05
Patent number
US07220752B2

Reaction notes

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