Hydrogen Bromide → Ethyl 2-(4-chlorophenoxy)-3-(4-hydroxyphenyl)propionate

HRID 1860073Notes

Reaction equation

HRID 1860073 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([O:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=1)C1C=CC=CC=1.Br.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([O:22][CH:16]([CH2:15][C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 11430Potassium CarbonateHCID 18625711Ethyl 3-(4-benzyloxyphenyl)-2-(4-chlorophenoxy)propionate

Product 1

HCID 18625838Ethyl 2-(4-chlorophenoxy)-3-(4-hydroxyphenyl)propionateYield 82.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a similar manner to that described in Reference example 37(b), a reaction was carried out using ethyl 3-(4-benzyloxyphenyl)-2-(4-chlorophenoxy)propionate (5.99 g), which is the product of Reference example 38(a), a solution of hydrogen bromide in acetic acid (25%, 60 ml) and potassium carbonate (4.68 g) and the reaction mixture was treated to afford the desired compound (3.85 g) as colorless crystals.

Sources & evidence

ORD record
ord-5a3f3151f41b40768c4535435257d232
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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