4-Iodophenol → HCID 67279307, compound

HRID 1694589Notes

Reaction equation

HRID 1694589 reaction equation
[C:1]([O:20][CH2:21][CH:22]([OH:44])[CH2:23][O:24][C:25]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:45][C:46]1[CH:51]=[CH:50][C:49](O)=[CH:48][CH:47]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[I:45][C:46]1[CH:51]=[CH:50][C:49]([O:44][CH:22]([CH2:21][O:20][C:1]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:23][O:24][C:25]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[CH:48][CH:47]=1

Participants

6

Reactant 4

HCID 108944-IodophenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2250771,3-Bis(triphenylmethoxy)propan-2-ol

Product 1

HCID 67279307HCID 67279307, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 1 (5.0 g, 8.67 mmol), 4-iodophenol (2.10 g, 9.54 mmol) and triphenyl phosphine (2.5 g, 9.5 mmol) were dissolved in dry THF (35 mL). Diisopropyl azodicarboxylate (1.88 mL, 9.5 mmol) was added dropwise during 15 min, and the reaction was allowed to proceed overnight at RT. All volatiles were removed in vacuo. Purification on silica gel (eluent, petroleum ether, bp 40-60° C.: dichloromethane, 1:1, v/v) yielded 6.07 g of the title compound. 1H NMR (CDCl3): 7.49 (2H, d, J 9.1); 7.37-7.21 (30H); 6.62 (2H, d, J 9.1). 4.43 (1H, m); 3.40 (4H, m).

Workup

  1. customAll volatiles were removed in vacuo
  2. customPurification on silica gel (eluent, petroleum ether, bp 40-60° C.

Sources & evidence

ORD record
ord-de98b9fafa9e4e4d93ce50296e9b0f8a
Source dataset
uspto-grants-2012_04
Patent number
US08158782B2

Reaction notes

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