Bromine → 5-Bromo-2-methyl-4-(5,6,7,8-tetrahydronaphthalen-2-yl)oxazole

HRID 350733Notes

Reaction equation

HRID 350733 reaction equation
[CH3:1][C:2]1[O:3][CH:4]=[C:5]([C:7]2[CH:16]=[CH:15][C:14]3[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=3[CH:8]=2)[N:6]=1.[Br:17]Br.C(=O)([O-])O.[Na+]>ClCCl>[Br:17][C:4]1[O:3][C:2]([CH3:1])=[N:6][C:5]=1[C:7]1[CH:16]=[CH:15][C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 230617572-Methyl-4-(5,6,7,8-tetrahydronaphthalen-2-yl)oxazole

Product 1

HCID 230619435-Bromo-2-methyl-4-(5,6,7,8-tetrahydronaphthalen-2-yl)oxazoleYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-methyl-4-(5,6,7,8-tetrahydronaphthalen-2-yl)oxazole (9.0 g) in dichloromethane (90 mL) was added dropwise a solution of bromine (2.2 mL) in dichloromethane (5 mL) at room temperature. After stirring the mixture at room temperature for 30 min, saturated aqueous sodium hydrogen carbonate was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and concentrated to give 5-bromo-2-methyl-4-(5,6,7,8-tetrahydronaphthalen-2-yl)oxazole (11.7 g, yield 95%) as crystals. Recrystallization from ethanol gave colorless plate crystals. melting point: 97–98° C.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6dd76135a9c34487a0a9881deac33fff
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

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