Iodine → (4'-Chloro-4-ethylbiphen-3-yl)furan-2-ylmethanol

HRID 40470Notes

Reaction equation

HRID 40470 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][CH3:9].[Mg].II.[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[CH:25]=[O:26]>O1CCCC1>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([C:4]2[CH:5]=[CH:6][C:7]([CH2:8][CH3:9])=[C:2]([CH:25]([C:21]3[O:20][CH:24]=[CH:23][CH:22]=3)[OH:26])[CH:3]=2)=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 807IodineHCID 7362FurfuralHCID 5462224Magnesium2×HCID 594459053-Bromo-4'-chloro-4-ethylbiphenyl2×

Product 1

HCID 58502794(4'-Chloro-4-ethylbiphen-3-yl)furan-2-ylmethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Approximately 10 ml of a solution of 3-bromo-4′-chloro-4-ethylbiphenyl (40.0 g, 135.3 mmol) in tetrahydrofuran (200 ml) is added to magnesium turnings in a dry flask, followed by a crystal of iodine. The mixture is allowed to stand without stirring for 30 minutes, then stirred once and warmed until the orange coloured mixture becomes colourless. The remainder of the 3-bromo-4′-chloro-4-ethylbiphenyl solution is added dropwise over 30 minutes with external heating applied as necessary to maintain a gentle reflux. Once the addition is complete, the mixture is heated to reflux for 2-3 hours, until only trace residues of magnesium remain. The mixture is cooled to room temperature, and then cooled further in an ice-bath. A solution of 2-furaldehyde (13.05 g, 135.8 mmol) in tetrahydrofuran (80 ml) is added dropwise over 35 minutes, and the mixture is stirred at room temperature overnight.

Workup

  1. stirringstirred once
  2. temperaturewarmed until the orange coloured mixture
  3. temperaturewith external heating
  4. temperatureto maintain a gentle reflux
  5. additionOnce the addition
  6. temperaturethe mixture is heated
  7. temperaturecooled further in an ice-bath
  8. stirringthe mixture is stirred at room temperature overnight

Sources & evidence

ORD record
ord-292f32fc9ab04384a8099dec217a1cbc
Source dataset
uspto-grants-2013_09
Patent number
US08530388B2

Reaction notes

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