Boron tribromide → 4-(1,3-Thiazol-2-yl)phenol

HRID 750086

Reaction equation

C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][CH:11]=[CH:12][N:13]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[S:10]1[CH:11]=[CH:12][N:13]=[C:9]1[C:6]1[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of the product of step 1 (1.0 g, 5.23 mmol) in methylene chloride (25 ml) was slowly added boron tribromide (2.00 ml, 15.7 mmol) at −78° C., and stirred at −78° C. for 1 h. After it was stirred at room temperature for 16 h, the reaction mixture was poured into ice-water. The product was collected on a filter, washed with ether to yield the title product (0.84 g, 84%); 1H NMR (400 MHz, CDCl3) δ 7.85 (d, J=3.2 Hz, 1H), 7.79 (d, J=8.8 Hz, 2H), 7.67 (d, J=3.2 Hz, 1H), 6.88 (d, J=8.8 Hz, 2H); MS (ESI−) 176 (M−1, 100).

Workup

customat −78° C.
stirringAfter it was stirred at room temperature for 16 h
customThe product was collected on a filter
washwashed with ether

Sources & evidence

ORD record: ord-7b15290911234000bd6b0a3b8966e127
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07402684B2

Linked notes

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