2-bromo-3-methyl-phenol

Step 12-Amino-m-cresol 8a (5.7 g, 46.3 mmol) is dissolved in H2-Amino-/77-cresol 8a (5.7 g, 46.3 mmol) is dissolved in H2-Amιno-/77-cresol 8a (5 7 g, 46 3 mmol) is dissolved in H2-Amino-m-cresol 8a (5.7 g, 46.3 mmol) is dissolved in HStep 12-Amino-m-cresol 8a (5.7 g, 46.3 mmol) is dissolved in H2O (30 mL) and 1 , 4-dioxan 2-Amino-/77-cresol 8a (5.7 g, 46.3 mmol) is dissolved in H2O (30 mL) and 1 , 4-dioxane (15 mL). The mixture is heated to reflux and then HBr (48%, 17 mL, 0.31 mol) is added dropwise over a period of about 20 min. The reflux is maintained for about an additional 15 min after the addition is complete. The reaction is cooled to O0C, and NaNO2 in H2O (20 mL) is added over a period of about 30 min. The stirring is continued for about 15 min at O0C, the mixture is then transferred in one shot to a stirring mixture of Cu(I)Br (7.64 g, 53.2 mmol, 1.15 eq) in H2O (20 mL) and HBr (48%, 17 mL, 0.31 mol) at O0C (protected from light). The reaction is stirred for about 15 min at O0C, is warmed to 6O0C, is stirred for an additional 15 min, is cooled to RT and is then stirred overnight. The reaction mixture is then transferred to a separatory funnel and extracted with EtOAc (3x). The organic layers are combined, washed with brine, dried over anhydrous MgSO4, filtered and concentrated over silica to afford a mixture that is purified using the CombiFlash Companion (20% EtOAc/hexanes) to afford the desired bromide 8b (1.46 g, 17% yield) as a red-brown oil.2-Amiotano-/77-cresol 8a (5 7 g, 46 3 mmol) is dissolved in H2O (30 ml_) and 1 , 4-diotaoxane (15 ml_) The mixture is heated to reflux and then HBr (48%, 17 ml_, 310 mmol) is added dropwise over a period of 20 mm The reflux is maintained for an additional 15 mm after the addition is complete The reaction is cooled to O0C, and NaNO2 in H2O (20 mL) is added over a period of 30 mm The stirring is continued for 15 mm at O0C, the mixture is then transferred in one shot to a stirring mixture of Cu(I)Br (7 64 g, 53 2 mmol) in H2O (20 mL) and HBr (48%, 17 mL, 310 mmol) at 00C (protected from light) The reaction is stirred for 15 mm at O0C, is warmed to 6O0C, is stirred for an additional 15 mm, is cooled to RT and is then stirred overnight The reaction mixture is then transferred to a separatory funnel and extracted with EtOAc (3x) The organic layers are combined, washed with brine, dried over anhydrous MgSO4, filtered and concentrated over silica to afford a mixture that is purified using the CombiFlash Companion (20% EtOAc/hexanes) to afford the desired bromide 8b (1 46 g, 17% yield) as a red-brown oil2-Amino-m-cresol 8a (5.7 g, 46.3 mmol) is dissolved in H2O (30 mL) and 1 , 4-dioxan (15 mL). The mixture is heated to reflux and then HBr (48%, 17 mL, 0.31 mol) is added dropwise over a period of 20 min. The reflux is maintained for an additional 15 min after the addition is complete. The reaction is cooled to O0C, and NaNO2 in H2O (20 mL) is added over a period of 30 min. The stirring is continued for 15 min at O0C, the mixture is then transferred in one shot to a stirring mixture of Cu(I)Br (7.64 g, 53.2 mmol) in H2O (20 mL) and HBr (48%, 17 mL, 0.31 mol) at O0C (protected from light). The reaction is stirred for 15 min at O0C, warmed to 6O0C, stirred for an additional 15 min, cooled to RT and then stirred overnight. The reaction mixture is then transferred to a separatory funnel and extracted with EtOAc (3x). The organic layers are combined, washed with brine, dried over anhydrous MgSO4, filtered and concentrated over silica to afford a mixture that is purified using the CombiFlash Companion (20% EtOAc/hexanes) to afford the desired bromide 8b (1.46 g, 17% yield) as a red-brown oil.

Molecular Weight:187.03
XLogP3:2.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:185.96803
Monoisotopic Mass:185.96803
Topological Polar Surface Area:20.2
Heavy Atom Count:9
Complexity:94.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes