1-(Chloromethyl)-2-iodobenzene → (3-Formyl-4-(2-iodo-benzyloxy)-phenyl)-acetic acid methyl ester

HRID 1433309

Reaction equation

HRID 1433309 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH:12]=[O:13])[CH:6]=1.Cl[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[I:23].N[C@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1>C(#N)C.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[I:23])=[C:7]([CH:12]=[O:13])[CH:6]=1

Participants

6

Reactant 3

HCID 1010641-(Chloromethyl)-2-iodobenzeneHCID 1859152-NaphthylalanineHCID 12374099Methyl 2-(3-formyl-4-hydroxyphenyl)acetate

Product 1

HCID 11682982(3-Formyl-4-(2-iodo-benzyloxy)-phenyl)-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent2×

Procedure

A solution of (3-formyl-4-hydroxy-phenyl)-acetic acid methyl ester (17.2 g, 85.9 mmol) in acetonitrile was slowly added to a solution of 1-chloromethyl-2-iodo-benzene (13.06 g, 94.5 mmol) and Nal (3.22 g, 21.5 mmol) in acetonitrile (273 ml) at reflux temperature and the mixture was mantained at this temperature for 3 hours. Once the mixture reached room temperature, the residue that had formed was filtered, washed with acetonitrile and concentrated to obtain a residue that was then dissolved in toluene (330 ml) and washed with NaOH 0.1N and water. The organic layer was concentrated to dryness, diluted with acetone (330 ml) and was stirred into water (500 ml) at room temperature. The mixture was filtered and washed with water to obtain 33.959 (96%) of [3-Formyl-4-(2-iodo-benzyloxy)-phenyl]-acetic acid methyl ester, which was purified by crystallization in toluene-cyclohexane (99% HPLC)

Workup

  1. temperatureat reflux temperature
  2. customreached room temperature
  3. customthe residue that had formed
  4. filtrationwas filtered
  5. washwashed with acetonitrile
  6. concentrationconcentrated
  7. customto obtain a residue that
  8. washwashed with NaOH 0.1N and water
  9. concentrationThe organic layer was concentrated to dryness
  10. additiondiluted with acetone (330 ml)
  11. filtrationThe mixture was filtered
  12. washwashed with water

Sources & evidence

ORD record
ord-6cdb77fceeb14b63b7ac2bc4f30fd8f5
Source dataset
uspto-grants-2009_11
Patent number
US07612219B2

Linked notes

Loading…