Bromine → (1-Oxo-2-bromo-2-ethyl-6,7-dichloro-5-indanyloxy)acetic acid

HRID 1834668Notes

Reaction equation

HRID 1834668 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:13][CH2:14][C:15]([OH:17])=[O:16])=[C:8]([Cl:12])[C:9]=2[Cl:11])[CH2:4][CH:3]1[CH2:18][CH3:19].[Br:20]Br.S(=O)(O)[O-].[Na+]>C(O)(=O)C.Br>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:13][CH2:14][C:15]([OH:17])=[O:16])=[C:8]([Cl:12])[C:9]=2[Cl:11])[CH2:4][C:3]1([Br:20])[CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 24408BromineHCID 33794Acetic acid, 6,7-dichloro-2-ethyl-1-oxo-5-indanyloxy-HCID 23665763Sodium Bisulfite

Product 1

HCID 20373915(1-Oxo-2-bromo-2-ethyl-6,7-dichloro-5-indanyloxy)acetic acidYield 97%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideCatalystHCID 176Acetic AcidSolvent2×

Procedure

To a stirred suspension of (1-oxo-2-ethyl-6,7-dichloro-5-indanyloxy)acetic acid (30.3 g., 0.10 moles) in acetic acid (300 ml.) is added a solution of bromine (16.0 g., 0.10 moles) in acetic acid (50 ml.) over a period of 30 minutes. The reaction is catalyzed by the addition of 48% aqueous hydrobromic acid (2 drops). The clear yellow solution is stirred at room temperature for 30 minutes then poured into ice water (1 l.) containing sodium bisulfite (2 g.). The crude (1-oxo-2-bromo-2-ethyl-6,7-dichloro-5-indanyloxy)acetic acid (36 g., 97%) thus obtained is filtered, washed with water and dried. It melts at 189°-191° C. after recrystallization from a mixture of ethyl acetate and hexane.

Sources & evidence

ORD record
ord-9157501c0de64555aa35d52bda3eca4b
Source dataset
uspto-grants-1978_01
Patent number
US04070539

Reaction notes

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