4-Toluenesulfonyl chloride → HCID 86599120, compound

HRID 2116009Notes

Reaction equation

HRID 2116009 reaction equation
C(C1C(F)=C(F)C=C(Br)C=1O)C=C.ClC1C=C(C=CC=1)C(OO)=O.C(=O)([O-])[O-].[K+].[K+].[Br:31][C:32]1[C:40]2[O:39][CH:38]([CH2:41][OH:42])[CH2:37][C:36]=2[C:35]([F:43])=[C:34]([F:44])[CH:33]=1.C(N(C(C)C)CC)(C)C.[C:54]1([CH3:64])[CH:59]=[CH:58][C:57]([S:60](Cl)(=[O:62])=[O:61])=[CH:56][CH:55]=1>CN(C)C1C=CN=CC=1>[CH3:64][C:54]1[CH:59]=[CH:58][C:57]([S:60]([O:42][CH2:41][CH:38]2[CH2:37][C:36]3[C:35]([F:43])=[C:34]([F:44])[CH:33]=[C:32]([Br:31])[C:40]=3[O:39]2)(=[O:62])=[O:61])=[CH:56][CH:55]=1

Participants

8

Reactant 6

HCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 81531DiisopropylethylamineHCID 22144872HCID 22144872, compoundHCID 68962568HCID 68962568, compound

Product 1

HCID 86599120HCID 86599120, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Treatment of 2-allyl-6-bromo-3,4-difluorophenol (5.0 g, 0.020 mol) with 3-chloroperoxybenzoic acid (77%, 8.1 g, 0.036 mol) followed by potassium carbonate (6.94 g, 0.050 mol) generally according to the procedure described for Intermediate 9 afforded (±)-(7-bromo-4,5-difluoro-2,3-dihydro-1-benzofuran-2-yl)methanol a brown oil. Treatment of the alcohol with diisopropylethylamine (2.57 g, 0.020 mol), p-toluenesulfonyl chloride (2.28 g, 0.012 mol), and 4-(dimethylamino)pyridine (0.29 g, 2.375 mmol) generally according to the procedure described for Intermediate 45 gave 2.9 g (35%) of (±)-(7-bromo-4,5-difluoro-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate as a white solid. Rf=0.46 (silica, ethyl acetate:hexanes 1:3); 1H NMR (DMSO-d6) δH 7.73 (d, 2H); 7.50 (dd, 1H); 7.43 (d, 2H); 5.15 (m, 1H); 4.3 (dd, 1H); 4.22 (dd, 1H); 3.45 (dd, 1H); 3.08 (dd, 1H).

Sources & evidence

ORD record
ord-f7f6e413a5944b7997524d7f2b0ec2ec
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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