4-Toluenesulfonyl chloride → (7-Bromo-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate

HRID 2115942Notes

Reaction equation

HRID 2115942 reaction equation
[Br:1][C:2]1[C:10]2[O:9][CH:8]([CH2:11][OH:12])[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>>[CH3:23][C:13]1[CH:18]=[CH:17][C:16]([S:19]([O:12][CH2:11][CH:8]2[CH2:7][C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([Br:1])[C:10]=3[O:9]2)(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 59858092HCID 59858092, compound

Product 1

HCID 58747572(7-Bromo-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonateYield 80.5%

Procedure

Treatment of (±)-(7-bromo-2,3-dihydro-1-benzofuran-2-yl)methanol (49.0 g, 0.214 mol) with p-toluenesulfonyl chloride (44.9 g, 0.235 mol) generally according to the procedure described for Intermediate 10 gave 66.00 g (80%) (±)-(7-bromo-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate as a white solid. Rf=0.44 (silica, ethyl acetate:hexanes 1:4); mp 120-122° C.; Anal. calcd. for C16H15BrO4S: C, 50.14; H, 3.94. Found: C, 48.47; H, 4.03.

Sources & evidence

ORD record
ord-27f5a71432dd435691f50f7629f21050
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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