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

HRID 398058Notes

Reaction equation

HRID 398058 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-4373544e45264bb59b9adcb73541a31d
Source dataset
uspto-grants-2003_08
Patent number
US06610744B2

Reaction notes

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