3-Methylbenzoyl chloride → HCID 10168177, compound

HRID 1352236Notes

Reaction equation

HRID 1352236 reaction equation
C[O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:10]=[C:9]([Br:11])[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([CH:21]([CH3:23])[CH3:22])[CH:14]=2)=[C:7]([Br:24])[CH:6]=1.[C:26]1([CH3:35])[CH:31]=[CH:30][CH:29]=[C:28]([C:32](Cl)=[O:33])[CH:27]=1>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[Br:24][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([OH:2])=[O:25])[CH:10]=[C:9]([Br:11])[C:8]=1[O:12][C:13]1[CH:14]=[C:15]([CH:21]([CH3:22])[CH3:23])[C:16]([O:19][CH2:20][CH2:6][C:5]([CH3:10])=[CH2:4])=[CH:17][C:18]=1[C:32](=[O:33])[C:28]1[CH:29]=[CH:30][CH:31]=[C:26]([CH3:35])[CH:27]=1

Participants

5

Reactant 2

HCID 743753-Methylbenzoyl chlorideHCID 11123548HCID 11123548, compound

Product 1

HCID 10168177HCID 10168177, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

TiCl4 (25.2 mL, 229 mmol) was added dropwise to a solution of 3,5-dibromo-4-(3-isopropyl-4 -methoxyphenoxy)phenylacetic acid methyl ester (31.0 g, 65.6 mmol) and m-toluoyl-chloride (35.4 g, 229 mmol) in CH2Cl2 (310 mL) at 0° C. The mixture was stirred at room temperature for 3 d, cooled to 0 C, and quenched with ice (300 g). The layers were separated and the aqueous phase was extracted with EtOAc (3×100 mL). The combined organic phases were washed with NaHCO3 (aq., sat, 3×100 mL), concentrated and purified by chromatography on silica gel to give 18.5 9 (49%) of the title compound.

Workup

  1. temperaturecooled to 0 C
  2. customquenched with ice (300 g)
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with EtOAc (3×100 mL)
  5. washThe combined organic phases were washed with NaHCO3 (aq., sat, 3×100 mL)
  6. concentrationconcentrated
  7. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-453ed12e10174b8b9f85f4f918cfe121
Source dataset
uspto-grants-2007_05
Patent number
US07220752B2

Reaction notes

Loading…