Potassium Carbonate → HCID 58516581, compound

HRID 1913852Notes

Reaction equation

HRID 1913852 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([Cl:13])=[CH:8][C:7]=1[I:14].[I:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[OH:23].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:13][C:9]1[CH:10]=[C:11]([CH3:12])[C:6]([O:5][CH2:4][CH2:3][CH2:2][O:23][C:17]2[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:16]=2[I:15])=[C:7]([I:14])[CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6202344-Chloro-2-iodophenolHCID 58516586HCID 58516586, compound

Product 1

HCID 58516581HCID 58516581, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 70 mL of acetone combine 4.08 g (10.48 mmol) of 2-(3-bromopropoxy)-5-chloro-1-iodo-3-methylbenzene, 2.67 g (10.49 mmol) of 2-iodo-4-chlorophenol (Prepared in a manner similar to Preparation 7) and 3.06 g (22.14 mmol) of potassium carbonate. Reflux overnight, filter, cool and concentrate to give an off white solid, which is crystallized using acetonitrile to yield 5.18 g (88%) of 5-chloro-2-(3-(4-chloro-2-iodophenoxy)propoxy)-1-iodo-3-methylbenzene as a white powder. 1H NMR (400 MHz, CDCl3) δ 7.74 (d, J=2.5 Hz, 1H), 7.58 (d, J=2.4 Hz, 1H), 7.31-7.23 (m, 1H), 7.16-7.10 (m, 1H), 6.76 (d, J=8.8 Hz, 1H), 4.28 (t, J=5.8 Hz, 2H), 4.09 (t, J=6.0 Hz, 2H), 2.36 (p, J=5.9 Hz, 2H), 2.26 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 156.17, 155.57, 138.56, 136.17, 133.37, 131.34, 129.89, 129.24, 126.36, 112.21, 92.21, 86.64, 68.85, 65.57, 29.85, 17.02. GCMS (m/e): 562 (M+).

Workup

  1. temperatureReflux overnight
  2. filtrationfilter
  3. temperaturecool
  4. concentrationconcentrate
  5. customto give an off white solid, which
  6. customis crystallized

Sources & evidence

ORD record
ord-de9ece54bb6f4cfa8d94526135b6777f
Source dataset
uspto-grants-2013_12
Patent number
US08609794B2

Reaction notes

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