(+/-)-(5-Chloro-7-methoxy-2-methyl-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate → HCID 86599126, compound

HRID 2116017Notes

Reaction equation

HRID 2116017 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C:13]2([CH3:25])[CH2:17][C:16]3[CH:18]=[C:19]([Cl:24])[CH:20]=[C:21]([O:22]C)[C:15]=3[O:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1>Br>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C:13]2([CH3:25])[CH2:17][C:16]3[CH:18]=[C:19]([Cl:24])[CH:20]=[C:21]([OH:22])[C:15]=3[O:14]2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 86599125(+/-)-(5-Chloro-7-methoxy-2-methyl-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 86599126HCID 86599126, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

Treatment of (±)-(5-chloro-7-methoxy-2-methyl-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (13.80 g, 0.036 mol) with hydrogen bromide (200 mL, 30 wt. % in acetic acid) generally according to the procedure described for Intermediate 46 afforded 11.7 g (80%) of (±)-(5-chloro-7-hydroxy-2-methyl-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate as a white solid. mp 135-137° C.; Anal. calcd. for C17H17ClO5S: C, 55.36; H, 4.65. Found: C, 54.35; H, 4.52.

Sources & evidence

ORD record
ord-d0cd274dccfa4893bae4f1ac2b995f08
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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