Chlorosulfonic acid → 4-(2-Bromo-4-(Trifluoromethyl)Phenyl)-3,4-Dihydro-2H-Benzo[B][1,4]Oxazine-7-Sulfonyl Chloride

HRID 528515

Reaction equation

HRID 528515 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[N:12]1[CH2:17][CH2:16][O:15][C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]1=2.[Cl:22][S:23](O)(=[O:25])=[O:24]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[N:12]1[CH2:17][CH2:16][O:15][C:14]2[CH:18]=[C:19]([S:23]([Cl:22])(=[O:25])=[O:24])[CH:20]=[CH:21][C:13]1=2

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 897615224-(2-Bromo-4-(Trifluoromethyl)Phenyl)-3,4-Dihydro-2H-Benzo[B][1,4]Oxazine

Product 1

HCID 897618504-(2-Bromo-4-(Trifluoromethyl)Phenyl)-3,4-Dihydro-2H-Benzo[B][1,4]Oxazine-7-Sulfonyl Chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of INTERMEDIATE B (1.325 g, 3.70 mmol) in DCM (7.40 mL) was cooled to 0° C. in an ice-water bath, and chlorosulfonic acid (1.230 mL, 18.50 mmol) was added dropwise. The resulting solution was stirred at RT for 4 hours until complete conversion to the desired product occurred. The reaction mixture was then slowly added dropwise to well-stirred ice water and subsequently neutralized to a pH of about 7 with saturated aqueous sodium bicarbonate solution. After extraction with EtOAc (×3), the combined organics were washed with water and brine, dried over magnesium sulfate, filtered and concentrated to provide INTERMEDIATE C. The material was taken forward without further purification. m/z (ESI) 477.8 (M+Na)+.

Sources & evidence

ORD record
ord-ac88c63dc2e9485a9fb6b6e97d4d2914
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Linked notes

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