Diethyl Ether → HCID 69751879, compound

HRID 2182122Notes

Reaction equation

HRID 2182122 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([C:17](=[O:27])[NH:18][C:19]2[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[CH:20]=2)[OH:16])=[CH:11][CH:10]=1)([CH3:7])[CH3:6])[CH3:2].[Pb](Br)(Br)[Br:30].C(Cl)Cl.C(O[CH2:39][CH3:40])C>>[CH2:1]([O:3][C:4](=[O:28])[C:5]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([Br:30])([C:17](=[O:27])[NH:18][C:19]2[CH:20]=[C:21]([CH3:26])[CH:22]=[C:23]([CH3:25])[CH:24]=2)[O:16][CH2:39][CH3:40])=[CH:13][CH:14]=1)([CH3:7])[CH3:6])[CH3:2]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 14455217HCID 14455217, compoundHCID 69751727HCID 69751727, compound

Product 1

HCID 69751879HCID 69751879, compound

Procedure

To a stirring solution of 2-{4-[(3,5-Dimethyl-phenylcarbamoyl)-hydroxy-methyl]-phenoxy}-2-methyl-propionic acid ethyl ester (1.4 g, 3.6 mmol), in dry diethyl ether (10 mL) under nitrogen at 0° C. was added lead tribromide in methylene chloride (4.4 mL, 4.4 mmol) drop wise. The reaction mixture was further stirred at room temperature for 4 hr and concentrated. Water (100 mL) added and the product extracted with Ethyl acetate (3×50 mL), dried and evaporated to yield 1.0 g of 2-{4-[bromo-(3,5-dimethyl-phenylcarbamoyl)-ethoxy-methyl]-phenoxy}-2-methyl-propionic acid ethyl ester.

Workup

  1. concentrationconcentrated
  2. additionWater (100 mL) added
  3. extractionthe product extracted with Ethyl acetate (3×50 mL)
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-0ec5933420d048a1b7a89522f2b20938
Source dataset
uspto-grants-2005_05
Patent number
US06894185B2

Reaction notes

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