Boron tribromide → HCID 9927408, compound

HRID 1450513Notes

Reaction equation

HRID 1450513 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([O:26]C)=[C:10]([CH:12]2[C:20]3[C:15](=[CH:16][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:18][CH:19]=3)[NH:14][C:13]2=[O:25])[CH:11]=1>C(Cl)Cl>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([OH:26])=[C:10]([CH:12]2[C:20]3[C:15](=[CH:16][C:17]([C:21]([F:23])([F:24])[F:22])=[CH:18][CH:19]=3)[NH:14][C:13]2=[O:25])[CH:11]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 10132132HCID 10132132, compound

Product 1

HCID 9927408HCID 9927408, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of BBr3 (12 mL, 12 mmol; 1M in CH2Cl2) was added to a stirred cold (-78° C.) solution of (±)-3-(5-chloro-2-methoxyphenyl)-1,3-dihydro-6-(trifluoromethyl)-2H-indol-2-one (1.37 g, 4 mmol) in anhydrous CH2Cl2 (20 mL). The mixture was allowed to warm to ambient temperature and maintained for 2 hours. The reaction was quenched with saturated NaHCO3 and then acidified with 1N HCl. The organic layer was separated, washed with water, brine and then dried (MgSO4). Evaporation of CH2Cl2 gave an off-white solid which was triturated with warm CH2Cl2 to afford the title compound (1.21 g, 93%): mp 266°-268° C.; IR (KBr, cm-1) 3320, 1690, 1310, 1250, 1160, 1125; 1H NMR (300 MHz, DMSO-d6)δ 4.85 (1 H, s), 6.75 (1 H, d, J=8.6 Hz), 7.04 (1 H, s), 7.11, (1 H, d, J=7.7 Hz), 7.17 (1 H, dd, J=8.6 and 2.6 Hz), 7.22 (1 H, d, J=8.0 Hz), 7.26 (1 H, d, J=2.4 Hz), 9.82 (1 H, s), 10.73 (1 H, s); 13C NMR (75 MHz, DMSO-d6)δ 48.47, 104.94, 116.84. 118.16, 122.27, 124.20, 125.61, 126.06, 128.05, 128.41, 130.76, 134.72, 143.69, 154.26, 176.92. MS m/e 328 (MH+).

Workup

  1. temperaturemaintained for 2 hours
  2. customThe reaction was quenched with saturated NaHCO3
  3. customThe organic layer was separated
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. customEvaporation of CH2Cl2
  7. customgave an off-white solid which
  8. customwas triturated with warm CH2Cl2

Sources & evidence

ORD record
ord-93fe0c419fc14a7b83ee298e84167cc5
Source dataset
uspto-grants-1997_02
Patent number
US05602169

Reaction notes

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