Tetrahydrofuran → HCID 12712286, compound

HRID 544413Notes

Reaction equation

HRID 544413 reaction equation
[C:1]1([CH3:12])[CH:6]=[CH:5][C:4]([S:7][CH2:8][C:9]([CH3:11])=[CH2:10])=[CH:3][CH:2]=1.C1COCC1.[Br:18]Br>>[C:1]1([CH3:12])[CH:2]=[CH:3][C:4]([S:7][CH2:8][CH:9]([CH3:11])[CH2:10][Br:18])=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24408BromineHCID 125911931-Methyl-4-[(2-methylprop-2-en-1-yl)sulfanyl]benzene

Product 1

HCID 12712286HCID 12712286, compound

Procedure

3-p-Tolylthio-2-methylpropene (15 mmol, 2.67 g) was hydroborated with BH3 -THF (5 mmol) at 0°. The brominations were carried out as described in the general procedure. The product was isolated via chromatography; yield 2.67 g (61%); [90% via Br2 reactions]; m.s. 257 and 259 [M-1] (calcd. 258 and 260); NMR (CDCl3) δ 1.0 (d, 3H, --CH3), 1.6 (m, 1H, --CH--), 2.2 (s,2H, ArCH3), 3.4 (m, 2H, --CH2Br), 3.2 (d, 2H, --SCH2), 7.0 (A'2X'2, 4H, ArH).

Workup

  1. customat 0°
  2. customThe product was isolated via chromatography

Sources & evidence

ORD record
ord-c8af02d5056a498cbf92ac9b1b4d5b0c
Source dataset
uspto-grants-1984_05
Patent number
US04450149

Reaction notes

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