4-Toluenesulfonyl chloride → HCID 86599167, compound

HRID 2116088Notes

Reaction equation

HRID 2116088 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]=[C:4]([C:13]([F:16])([F:15])[F:14])[CH:3]=1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>>[CH3:27][C:17]1[CH:22]=[CH:21][C:20]([S:23]([O:12][CH2:11][CH:8]2[CH2:7][C:6]3[CH:5]=[C:4]([C:13]([F:16])([F:14])[F:15])[CH:3]=[C:2]([Br:1])[C:10]=3[O:9]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 68961966HCID 68961966, compound

Product 1

HCID 86599167HCID 86599167, compoundYield 70%

Procedure

Treatment of (±)-[7-bromo-5-(trifluoromethyl)-2,3-dihydro-1-benzofuran-2-yl]methanol (3.59 g, 12.1 mmol) with p-toluenesulfonyl chloride (3.6 g, 18.2 mmol) generally according to described for Intermediate 10 provided 3.82 g (70%) (±)-[7-bromo-5-(trifluoromethyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate. mp 95-97° C.

Sources & evidence

ORD record
ord-13b4bab94e5d476b821df3a619a83bb5
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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