Hydrochloric Acid → HCID 19799667, compound

HRID 2081275Notes

Reaction equation

HRID 2081275 reaction equation
[Mg].II.Br[CH2:5][CH3:6].Cl[C:8]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][C:9]=1[O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:16](=[O:17])[O:15][C:14]2(O)[CH3:21].[ClH:31]>C(OCC)C>[Cl:31][C:8]1[CH:26]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:24]=[CH:23][C:9]=1[O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:16](=[O:17])[O:15][C:14]2([CH2:5][CH3:6])[CH3:21]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 6332Ethyl BromideHCID 5462224MagnesiumHCID 11068325HCID 11068325, compound

Product 1

HCID 19799667HCID 19799667, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

Magnesium (1.44 g, 0.06 mol) suspended in diethyl ether (20 ml), was treated with a crystal of iodine, then a solution of bromoethane (6.54 g, 0.06 mol) in diethyl ether (15 ml) was added dropwise over 30 minutes. Reflux was maintained throughout this period by the heat of reaction. The mixture was stirred for 45 minutes before a solution of 5-(2-chloro-4-trifluoromethylphenoxy)-3-hydroxy-3-methylphthalide (5.38 g, 0.015 mol) dissolved in diethyl ether (20 ml) was added over 20 minutes. After stirring for a further 40 minutes, 50% hydrochloric acid (12 ml) was cautiously added, then the phases separated. The organic phase was washed with water 3×15 ml), the solvent stripped off and the residual oil distilled.

Workup

  1. temperatureReflux
  2. temperaturewas maintained throughout this period by the
  3. temperatureheat of reaction
  4. additionwas added over 20 minutes
  5. customthe phases separated
  6. washThe organic phase was washed with water 3×15 ml), the solvent
  7. distillationthe residual oil distilled

Sources & evidence

ORD record
ord-7ada10c80c344c9eb1321e693149ce97
Source dataset
uspto-grants-1993_02
Patent number
US05183907

Reaction notes

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