Busulfan → 7-Bromo-5-[(4-methylphenyl)sulfonyl]-2,3-dihydro-1-benzofuran

HRID 1162088

Reaction equation

HRID 1162088 reaction equation
[Br:1][C:2]1[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.O.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](O)(=[O:20])=[O:19])=[CH:14][CH:13]=1.CS(OCCCCOS(C)(=O)=O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>>[Br:1][C:2]1[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([S:18]([C:15]2[CH:16]=[CH:17][C:12]([CH3:22])=[CH:13][CH:14]=2)(=[O:20])=[O:19])[CH:3]=1

Participants

5

Reactant 4

HCID 2478BusulfanHCID 14812Phosphorus oxide (P4O10)HCID 521998p-Toluenesulfonic acid monohydrateHCID 225718697-Bromo-2,3-dihydro-1-benzofuran2×

Product 1

HCID 668942287-Bromo-5-[(4-methylphenyl)sulfonyl]-2,3-dihydro-1-benzofuranYield 113.2%

Procedure

7-Bromo-1,2-dihydrobenzofuran (64 mg, 0.3 mmol; Intermediate 77) and para-toluenesulfonic acid monohydrate (62 mg, 0.3 mmol) were mixed and then a 1:10 mixture (by weight) of methanesulfonic and phosphorous pentoxide (1 mL) was added. The resultant mixture was stirred over night at room temperature and was then poured onto ice/water. The obtained crystalline material was filtered and dried to give 120 mg of the title product. 1H NMR (400 MHz, CDCl3) δ 2.40 (s, 3H), 3.33 (t, 2H), 4.73 (t, 2H), 7.29 (d, 2H), 7.65 (d, 1H), 7.79 (d, 2H), 7.89 (d, 1H); GC-MS (EI+) for C15H13BrSO3 m/z 354 (M+H)+.

Workup

  1. additionwas then poured onto ice/water
  2. filtrationThe obtained crystalline material was filtered
  3. customdried

Sources & evidence

ORD record
ord-12b7bb31c2e6447a8bb426a1da7329a7
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Linked notes

Loading…