Iodine → HCID 21514907, compound

HRID 1576263Notes

Reaction equation

HRID 1576263 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5](Br)[CH:6]=[CH:7][CH:8]=1.[Mg].II.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=[O:21].[Cl-].[NH4+]>CCOCC>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]([OH:21])[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:11])([F:10])[F:1])[CH:4]=1

Participants

7

Reactant 5

HCID 807IodineHCID 9817Benzene, 1-bromo-3-(trifluoromethyl)-2×HCID 115693-Methoxybenzaldehyde2×HCID 25517Ammonium ChlorideHCID 5462224Magnesium

Product 1

HCID 21514907HCID 21514907, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

m-Trifluoromethylbromobenzene (48 g.) in dry ether (160 ml.) is added dropwise and with stirring to magnesium turnings (5.2 g.) just covered with dry ether. After the addition of the first 10 ml. of solution, reaction is initiated by introduction of a crystal of iodine and the addition is then continued at such a rate as to maintain gentle refluxing. When all the m-trifluoromethylbromobenzene has been added and the reaction has subsided, m-methoxybenzaldehyde (27.2 g.) in dry ether (160 ml.) is added dropwise to the stirred Grignard reagent at such a rate as to maintain gentle refluxing. When all the m-methoxybenzaldehyde has been added, the reaction mixture is heated under reflux for 2 hours and then allowed to cool. Excess saturated aqueous ammonium chloride is added, the ethereal layer is separated, washed with water and with brine, dried (MgSO4) and the ether evaporated to give an oil which crystallises and is recrystallised from petroleum ether (b.p. 40°-60°C.) to give 3-methoxy-3'-trifluoromethylbenzhydrol, m.p. 51°-52°C.

Workup

  1. additionAfter the addition of the first 10 ml
  2. customof solution, reaction
  3. additionthe addition
  4. temperatureto maintain gentle refluxing
  5. temperatureto maintain gentle refluxing
  6. temperaturethe reaction mixture is heated
  7. temperatureunder reflux for 2 hours
  8. temperatureto cool
  9. customthe ethereal layer is separated
  10. washwashed with water and with brine
  11. dry with materialdried (MgSO4)
  12. customthe ether evaporated
  13. customto give an oil which
  14. customcrystallises
  15. customis recrystallised from petroleum ether (b.p. 40°-60°C.)

Sources & evidence

ORD record
ord-620b16b6396a4d538ea38da5d7a4599c
Source dataset
uspto-grants-1976_09
Patent number
US03979513

Reaction notes

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