Boron tribromide → 4-(5-Amino-4-methylisothiazol-3-yl)phenol

HRID 2422703

Reaction equation

HRID 2422703 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:17]([CH3:18])=[C:16]([NH2:19])[S:15][N:14]=2)=[CH:9][CH:8]=1>ClCCl>[NH2:19][C:16]1[S:15][N:14]=[C:13]([C:10]2[CH:11]=[CH:12][C:7]([OH:6])=[CH:8][CH:9]=2)[C:17]=1[CH3:18]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 534010803-(4-Methoxyphenyl)-4-methyl-1,2-thiazol-5-amine

Product 1

HCID 1363552854-(5-Amino-4-methylisothiazol-3-yl)phenolYield 106.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add boron tribromide (0.227 g, 0.909 mmol) to a solution of 3-(4-methoxy-phenyl)-4-methylisothiazol-5-ylamine (0.100 g, 0.455 mmol) in dichloromethane (5 mL) at −20° C. Stir and allow to warm to room temperature. Stir 4 h and quench with 1 N HCl. Extract with EtOAc (2 times 50 mL). Dry (MgSO4) and evaporate. The product is used for the next step without further purification. Yield: 106.8% ES-MS: m/e 207.0 (m+1).

Workup

  1. stirringStir 4 h
  2. customquench with 1 N HCl
  3. extractionExtract with EtOAc (2 times 50 mL)
  4. dry with materialDry (MgSO4)
  5. customevaporate
  6. customThe product is used for the next step without further purification

Sources & evidence

ORD record
ord-5d928e812cb34a688f8e133b726e02c0
Source dataset
uspto-grants-2011_06
Patent number
US07960419B2

Linked notes

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