Ammonium Chloride → 6-Iodo-4-methylchroman-4-ol

HRID 1985052Notes

Reaction equation

HRID 1985052 reaction equation
[Li][CH3:2].[Li+].[Br-].[I:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][CH2:11][CH2:10][C:9]2=[O:16].[NH4+].[Cl-]>O.C1COCC1>[I:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][CH2:11][CH2:10][C:9]2([CH3:2])[OH:16]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 82050Lithium BromideHCID 35802626-Iodochroman-4-oneHCID 178418348HCID 178418348, compound

Product 1

HCID 602068356-Iodo-4-methylchroman-4-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

CeCl3 (4.9 g, 19.8 mmol) was dried in vacuo at 140° C. for 3 h and then slurried with dry THF (100 ml) for 1 h. The white suspension was chilled to −78° C. followed by the addition of MeLi.LiBr (14.2 ml, 21.4 mmol) over 15 minutes. The mixture was stirred for 30 min followed by the addition of a THF (20 ml) solution of 6-iodo-2,3-dihydro-4H-chromen-4-one dropwise via syringe. After 30 min TLC (15% EtOAc/hexanes) indicated complete reaction. The mixture was treated with NH4Cl (aq.) 30 ml and diluted with water 150 ml. The mixture was extracted with EtOAc and the organic layer dried over Na2SO4. The Na2SO4 was removed by filtration and the filtrate concentrated in vacuo to yield 6-iodo-4-methylchroman-4-ol as an off white solid 4.7 g (95%). HRMS (ESI+) calcd for C10H11IO2 m/z 289.9806 (M+H)+. Found 289.9803.

Workup

  1. customreaction
  2. extractionThe mixture was extracted with EtOAc
  3. dry with materialthe organic layer dried over Na2SO4
  4. customThe Na2SO4 was removed by filtration
  5. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-a823cfcbf28e430f953aad2b61290b0f
Source dataset
uspto-grants-2009_06
Patent number
US07544717B2

Reaction notes

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