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

HRID 1669508Notes

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 from step 2 (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 product from step two (0.84 g, 84%). 1HNMR (400 MHz, CDCl3) δ 6.88 (d, J=8.8 Hz, 2H), 7.67 (d, J=3.2 Hz, 1H), 7.79 (d, J=8.8 Hz, 2H), 7.85 (d, J=3.2 Hz, 1H), MS (ESI−) m/z 176 (M−1).

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-6cf63859ede545348979f087c5a33e73
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989480B2

Reaction notes

Loading…