Hydrogen Bromide → HCID 86637553, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]([CH2:16][C:17]([OH:19])=O)[C:9]=2[F:20])[CH:5]=[CH:6][CH:7]=1.Cl[CH:22](Cl)C.S(Cl)(Cl)=O.C[Si](C=[N+]=[N-])(C)C.[BrH:36].C([O-])([O-])=O.[Na+].[Na+]>ClCCl>[Br:36][CH2:22][C:17](=[O:19])[CH2:16][C:10]1[C:9]([F:20])=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[C:13]([O:14][CH3:15])=[CH:12][CH:11]=1Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Into a 20 mL vial with stir bar was added (3′-Chloro-2-fluoro-6-methoxy-biphenyl-3-yl)-acetic acid (I-74, R1=Me, Y═F) (306 mg, 1.04 mmol), dichloroethane (4 mL), thionyl chloride (151 uL, 2.08 mmol) and the solution was stirred at 80° C. for 1 hour. The solution was cooled to 0° C., 4 mL of dichloromethane were added, and a solution of (trimethylsilyl)diazomethane (1.56 mL, 3.11 mmol, 2.0 M in ether) was added and the reaction stirred at room temperature for 16 hours. The reaction was cooled to 0° C. and 0.5 mL HBr (48% in H2O) was added. After 30 minutes at 0° C., Na2CO3 was added until bubbling ceased and the reaction was dried by the addition of Na2SO4. The suspension was filtered and concentrated to yield product (390 mg, 99%) as a brown oil, which was used as is.
Workup
- stirringthe solution was stirred at 80° C. for 1 hour
- stirringthe reaction stirred at room temperature for 16 hours
- temperatureThe reaction was cooled to 0° C.
- customuntil bubbling
- dry with materialthe reaction was dried by the addition of Na2SO4
- filtrationThe suspension was filtered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-ad61c8601aa6426ea15f95e817b747da
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08791267B2
Reaction notes
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