Bromine → 4-(5-Bromo-4-tert-butylthiazol-2-yl)-3-methylbenzoic acid

HRID 531254Notes

Reaction equation

HRID 531254 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]=2[CH3:19])[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[Br:20]Br.S(=O)(O)[O-].[Na+]>C(O)(=O)C>[Br:20][C:9]1[S:8][C:7]([C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]=2[CH3:19])=[N:6][C:5]=1[C:1]([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24408BromineHCID 23665763Sodium BisulfiteHCID 900091344-(4-tert-Butylthiazol-2-yl)-3-methylbenzoic acid

Product 1

HCID 900091134-(5-Bromo-4-tert-butylthiazol-2-yl)-3-methylbenzoic acidYield 94%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-(4-tert-Butylthiazol-2-yl)-3-methylbenzoic acid (Step B, 7.0 g, 25.4 mmol) was dissolved in 30 mL of acetic acid, and bromine (8.1 g, 50.8 mmol) was added. The red mixture was stirred at room temperature for 20 minutes to see complete conversion by LCMS. Excess sodium bisulfite was added until the reaction mixture became colorless. The mixture was concentrated to dryness, dry-loaded to a silica gel column, and purified, eluting with 10% methanol in methylene chloride, to get 4-(5-bromo-4-tert-butylthiazol-2-yl)-3-methylbenzoic acid as a white solid (8.5 g, 94% yield over 2 steps). LCMS (M+H)+: 355.9; 353.9. 1H NMR (CDCl3, 500 MHz): 7.92 (s, 1H), 7.84 (m, 2H), 2.60 (s, 3H), 1.49 (s, 9H).

Workup

  1. concentrationThe mixture was concentrated to dryness, dry-loaded to a silica gel column
  2. custompurified
  3. washeluting with 10% methanol in methylene chloride

Sources & evidence

ORD record
ord-5ee6b680d64045e4b1528a8ad61d32e7
Source dataset
uspto-grants-2016_05
Patent number
US09353101B2

Reaction notes

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