Bromine → 5-(5-Bromo-thiazol-2-yl)-2-isopropoxybenzonitrile

HRID 1942637Notes

Reaction equation

[CH3:1][CH:2]([O:4][C:5]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][CH:15]=[CH:16][N:17]=2)=[CH:9][C:6]=1[C:7]#[N:8])[CH3:3].C([O-])(=O)C.[Na+].[Br:23]Br>C(O)(=O)C>[Br:23][C:15]1[S:14][C:13]([C:10]2[CH:11]=[CH:12][C:5]([O:4][CH:2]([CH3:1])[CH3:3])=[C:6]([CH:9]=2)[C:7]#[N:8])=[N:17][CH:16]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 2-[(1-methylethyl)oxy]-5-(1,3-thiazol-2-yl)benzonitrile (D64) (215 mg) and sodium acetate (144 mg) in acetic acid (8 mL) stirred at room temperature was added a solution of Br2 (0.045 mL) in acetic acid (1 mL) dropwise. The reaction mixture was stirred at 20° C. until start material was consumed completely. The reaction mixture was basified with 2M NaOH, then diluted with ethyl acetate. The mixture was washed with water and brine. The organic phase was dried over anhydrous sodium sulphate. After concentration, the crude product 5-(5-bromo-1,3-thiazol-2-yl)-2-[(1-methylethyl)oxy]benzonitrile (D65) (320 mg) was used for next step without further purification. δH (CDCl3, 600 MHz): 1.36 (6H, d), 4.65 (1H, m), 6.95 (1H, d), 7.64 (1H, s), 7.92 (1H, d), 7.97 (1H, dd).

Workup

customwas consumed completely
additiondiluted with ethyl acetate
washThe mixture was washed with water and brine
dry with materialThe organic phase was dried over anhydrous sodium sulphate
concentrationAfter concentration
customthe crude product 5-(5-bromo-1,3-thiazol-2-yl)-2-[(1-methylethyl)oxy]benzonitrile (D65) (320 mg) was used for next step without further purification

Sources & evidence

ORD record: ord-2cb45aae571f42b9af11281a84663bb9
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389508B2

Reaction notes

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