Hydrogen Bromide → HCID 86599076, compound

HRID 2115940Notes

Reaction equation

HRID 2115940 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH:13]2[CH2:17][C:16]3[CH:18]=[CH:19][CH:20]=[C:21]([O:22]C)[C:15]=3[O:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Br>O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][CH:13]2[CH2:17][C:16]3[CH:18]=[CH:19][CH:20]=[C:21]([OH:22])[C:15]=3[O:14]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 19886353HCID 19886353, compound

Product 1

HCID 86599076HCID 86599076, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To (±)-(7-methoxy-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (10.00 g, 0.030 mol) was added hydrogen bromide (20 mL, 30 wt. % in acetic acid) and the resulting solution was heated to 40° C. The reaction mixture was allowed to stir at 40° C. for 4 h. The reaction mixture was cooled to room temperature and was diluted with water (250 mL) and extracted with diethyl ether (3×200 mL). The combined organic extracts were washed with saturated sodium bicarbonate (3×300 mL), water (200 mL), and saturated aqueous sodium chloride (200 mL), were dried (magensium sulfate), and the solvent was removed in vacuo to provide a crude oil. Purification by flash column chromatography (silica, ethyl acetate:hexanes 1:3) provided 7.34 g (77%) of (±)-(7-hydroxy-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate as white solid. Rf=0.31 (silica, ethyl acetate:hexanes 1:3); mp 122-125° C.; Anal. calcd. for C16H16O5S: C, 59.99; H, 5.03. Found: C, 59.8; H, 4.73.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with diethyl ether (3×200 mL)
  3. washThe combined organic extracts were washed with saturated sodium bicarbonate (3×300 mL), water (200 mL), and saturated aqueous sodium chloride (200 mL)
  4. dry with materialwere dried (magensium sulfate)
  5. customthe solvent was removed in vacuo
  6. customto provide a crude oil
  7. customPurification by flash column chromatography (silica, ethyl acetate:hexanes 1:3)

Sources & evidence

ORD record
ord-ccf4ebc00817484d87cc3d211a4a743c
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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