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

HRID 1861883Notes

Reaction equation

HRID 1861883 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>>[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

4

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%

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-135e1a88e11f4537b648f4b169ef6620
Source dataset
uspto-grants-2003_03
Patent number
US06534544B1

Reaction notes

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