Iodine → 4-Bromo-2-iodo-1-methylbenzene

HRID 2039413Notes

Reaction equation

I([O-])(=O)(=O)=O.[Na+].[I:7]I.S(=O)(=O)(O)O.[Br:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1>C(O)(=O)C.C(OC(=O)C)(=O)C.O>[I:7][C:19]1[CH:20]=[C:15]([Br:14])[CH:16]=[CH:17][C:18]=1[CH3:21]

Participants

Conditions

Temperature: 10 °C

Procedure

Sodium periodate (0.5 molar equivalent, 102.5 g, 0.48 mol) and iodine (0.3 molar equivalent, 81.6 g, 0.32 mol) are suspended in acetic acid (700 ml) and acetic anhydride (340 ml). The batch is then cooled to 10° C., and sulfuric acid (2.9 molar equivalents, 142 ml, 2.66 mol) is slowly added dropwise at this temperature. 4-Bromotoluene 5 (1 molar equivalent, 160.7 g, 0.94 mol) is subsequently slowly added dropwise at room temperature, and the batch is stirred overnight. After addition of cooled water (1000 ml) and a solution of Na2SO3 (169 g in 1000 ml), the mixture is extracted by shaking with dichloromethane (DCM). The organic phase is washed with water, dried and evaporated in a rotary evaporator. The product 6 (188.0 g, 67%) is obtained in the form of a liquid by vacuum distillation.

Workup

extractiona solution of Na2SO3 (169 g in 1000 ml), the mixture is extracted
stirringby shaking with dichloromethane (DCM)
washThe organic phase is washed with water
customdried
customevaporated in a rotary evaporator

Sources & evidence

ORD record: ord-a29068e99bac4ee09e9a0fe49fd3508e
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580395B2

Reaction notes

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