Iodine chloride → 8Iodo-2,2,4,4-tetramethy-6-chromanoic Acid

HRID 1955311Notes

Reaction equation

HRID 1955311 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:14]([OH:16])=[O:15])[CH:8]=2)[O:3]1.[I:18]Cl.BrC1C=C(C(O)=O)C=C2C=1OC(C)(C)CC2(C)C>CC(O)=O>[I:18][C:5]1[CH:6]=[C:7]([C:14]([OH:16])=[O:15])[CH:8]=[C:9]2[C:4]=1[O:3][C:2]([CH3:17])([CH3:1])[CH2:11][C:10]2([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 24640Iodine chlorideHCID 157287092,2,4,4-Tetramethyl-3,4-dihydro-2H-1-benzopyran-6-carboxylic acidHCID 158405358-Bromo-2,2,4,4-tetramethyl-6-chromanoic acid2×

Product 1

HCID 230017638Iodo-2,2,4,4-tetramethy-6-chromanoic AcidYield 106.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2,2,4,4-tetramethyl-6-chromanoic acid (66 mg, 0.28 mmol) in 0.8 ml of AcOH was added ICl (0.07 ml, 1.4 mmol). The resulting colored solution was stirred at room temperature for overnight. Following the same procedure as for the synthesis of 8-bromo-2,2,4,4-tetramethyl-6-chromanoic acid (Compound P), the reaction gave the title compound (107 mg) as white solids.

Sources & evidence

ORD record
ord-1569996f4ea048019fab567e8dd32348
Source dataset
uspto-grants-2000_09
Patent number
US06124455

Reaction notes

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