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

HRID 2115930Notes

Reaction equation

C(C1C=CC(Br)=CC=1O)C=C.ClC1C=C(C=CC=1)C(OO)=O.C(=O)([O-])[O-].[K+].[K+].[Br:29][C:30]1[C:35]2[CH2:36][CH:37]([CH2:39][OH:40])[O:38][C:34]=2[CH:33]=[CH:32][CH:31]=1.[C:41]1([CH3:51])[CH:46]=[CH:45][C:44]([S:47](Cl)(=[O:49])=[O:48])=[CH:43][CH:42]=1>>[CH3:51][C:41]1[CH:46]=[CH:45][C:44]([S:47]([O:40][CH2:39][CH:37]2[CH2:36][C:35]3[C:30]([Br:29])=[CH:31][CH:32]=[CH:33][C:34]=3[O:38]2)(=[O:49])=[O:48])=[CH:43][CH:42]=1

Participants

Reactant 5

HCID 73974-Toluenesulfonyl chloride

HCID 11430Potassium Carbonate

HCID 70297m-Chloroperbenzoic acid

HCID 153607582-Allyl-5-bromophenol

HCID 21604503(4-Bromo-2,3-dihydrobenzofuran-2-yl)methanol

Product 1

HCID 86599073(+/-)-(4-Bromo-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonateYield 78%

Procedure

Treatment of 2-allyl-5-bromophenol (27.25 g, 0.128 mmol), with 3-chloroperoxybenzoic acid (66.20 g, 0.384 mol, 77%)) followed by potassium carbonate (44.18 g, 0.319 mol) generally according to the procedure described for Intermediate 9 provided (±)-(4-bromo-2,3-dihydro-1-benzofuran-2-yl)methanol as a yellow oil. Treatment of the oil with p-toluenesulfonyl chloride (15.65 g, 0.082 mol) generally according to the procedure described for Intermediate 10 afforded 24.7 g (78%) of (±)-(4-bromo-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate as a white solid. mp 90-91° C.; Anal. calcd. for C16H15BrO4S: C, 50.14; H, 3.94. Found: C, 50.09; H, 3.82.

Sources & evidence

ORD record: ord-b185bd909cff465fb2a11facdb5a0b7b
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07435837B2

Reaction notes

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