2-Bromo-4-tert-butyl-1-iodo-benzene synthesis

Yield:860435-39-8 92%

Reaction Conditions:

Stage #1: 2-bromo-4-tert-butylanilinewith hydrogenchloride;sodium nitrite in water;acetonitrile at 0 - 5; for 0.5 h;Sandmeyer Reaction;
Stage #2: with potassium iodide in water;acetonitrile at 20;Sandmeyer Reaction;

Steps:

1) 2-bromoiodobenzene (2a) as general procedure

General procedure: To a solution of 2-bromoaniline (5 g, 29 mmol) dissolved in CH3CN (80 mL) was added aq. HCl (15 mL conc. HCl in 50 mL water), then the mixture was cooled to 0 °C, and it was added a solution of NaNO2 (2.4 g, 34.87 mmol) in water (50 mL). After addition, the reaction was kept at the temperature lower than 5 °C for 30 min and it was added a solution of (7.23 g, 43.59 mmol) in water (50 mL). After addition, the reaction was kept at room temperature overnight, poured into water (300 mL) and extracted with CH2Cl2.The organic phase was dried over MgSO4. After workup, the brown oily product was distilled to afford a pale-yellow.

References:

Lv, Jun;Liu, Qiancai;Tang, Jie;Perdih, Franc;Kranjc, Kristof [Tetrahedron Letters,2012,vol. 53,# 39,p. 5248 - 5252] Location in patent:supporting information