Hydrogen Bromide → [1-Oxo-2-(4-hydroxyphenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid

HRID 839680Notes

Reaction equation

HRID 839680 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][C:3]1([C:19]1[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=1)[CH3:18].Br>C(O)(=O)C>[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([C:19]1[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=1)[CH3:18]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 12423617[1-Oxo-2-(4-methoxyphenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid

Product 1

HCID 12423618[1-Oxo-2-(4-hydroxyphenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred mixture of [1-oxo-2-(4-methoxyphenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid (1.80 g., 0.0046 mole), Example 8, Step E, 48% hydrobromic acid (50 ml.) and acetic acid (50 ml.) is heated at reflux for one hour, then poured into crushed ice-water (800 ml.) to precipitate 900 mg. of [1-oxo-2-(4-hydroxyphenyl)-2-methyl-6,7-dichloro-5-indanyloxy]-acetic acid which melts at 220°-222° C. after crystallization from acetic acid:water, 1:1, and nitromethane.

Workup

  1. temperatureis heated
  2. temperatureat reflux for one hour
  3. additionpoured
  4. customto precipitate 900 mg
  5. customof [1-oxo-2-(4-hydroxyphenyl)-2-methyl-6,7-dichloro-5-indanyloxy]-acetic acid which melts at 220°-222° C. after crystallization from acetic acid

Sources & evidence

ORD record
ord-c60dd06bfdaa48bfb4a1067a805e2cea
Source dataset
uspto-grants-1978_06
Patent number
US04096267

Reaction notes

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