Boron tribromide → HCID 9927408, compound

HRID 865235Notes

Reaction equation

HRID 865235 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 (1H, s), 6.75 (1H, d, J=8.6 Hz), 7.04 (1H, s), 7.11, (1H, d, J=7.7 Hz), 7.17 (1H, dd, J=8.6 and 2.6 Hz), 7.22 (1H, d, J=8.0 Hz), 7.26 (1H, d, J=2.4 Hz), =9.82 (1H, s), 10.73 (1H, 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-0fd8e2df61cd4a1791122e2e1082fdb3
Source dataset
uspto-grants-1996_10
Patent number
US05565483

Reaction notes

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