Boron tribromide → HCID 18430729, compound

HRID 1954299Notes

Reaction equation

HRID 1954299 reaction equation
[CH2:1]([C:8]1[S:9][C:10]([CH3:28])=[C:11]([CH3:27])[C:12]=1[C:13]([C:15]1[CH:20]=[C:19]([CH2:21][CH3:22])[C:18]([O:23]C)=[C:17]([CH2:25][CH3:26])[CH:16]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>>[CH3:28][C:10]1[S:9][C:8]2[CH:1]=[C:2]3[C:3](=[C:13]([C:15]4[CH:20]=[C:19]([CH2:21][CH3:22])[C:18]([OH:23])=[C:17]([CH2:25][CH3:26])[CH:16]=4)[C:12]=2[C:11]=1[CH3:27])[CH:4]=[CH:5][CH:6]=[CH:7]3

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 18430717HCID 18430717, compound

Product 1

HCID 18430729HCID 18430729, compound

Procedure

The title compound was prepared according to the procedure in Example 1, step 5, using (2-benzyl-4,5-dimethylthiophen-3-yl)-(3,5-diethyl-4-methoxy-phenyl)-methanone (17.67 g, 45.0 mmol) and boron tribromide (12.8 mL, 0.135 mol) to give 16.63 g, of the title compound. 1H NMR (DMSO-d6) δ 1.15 (t, 6 H), 1.61 (s, 3 H), 2.40 (s, 3 H), 2.59-2.73 (m, 4 H), 6.86 (s, 2 H), 7.32 (ddd, 1 H), 7.42 (ddd, 1 H), 7.47 (d, 1 H), 7.93 (d, 1 H), 8.31 (s, 1 H), 8.41 (s, 1 H). mass spectrum (+ESI) m/z 360 (M+).

Workup

  1. customThe title compound was prepared
  2. customto give 16.63 g

Sources & evidence

ORD record
ord-236034852c1e49e2b6982cd1cf2d613c
Source dataset
uspto-grants-2000_09
Patent number
US06121271

Reaction notes

Loading…