Boron tribromide → HCID 136350293, compound

HRID 1506387Notes

Reaction equation

HRID 1506387 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[C:12]1[O:11][C:10]([C:16]3[O:20][N:19]=[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:17]=3[C:27]([F:30])([F:29])[F:28])=[N:9][C:8]=1[CH2:7][CH2:6]2.B(Br)(Br)Br>ClCCl>[C:21]1([C:18]2[C:17]([C:27]([F:30])([F:29])[F:28])=[C:16]([C:10]3[O:11][C:12]4[C:13]5[C:5](=[CH:4][C:3]([OH:2])=[CH:15][CH:14]=5)[CH2:6][CH2:7][C:8]=4[N:9]=3)[O:20][N:19]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68182134HCID 68182134, compound

Product 1

HCID 136350293HCID 136350293, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To solution of 7-methoxy-2-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[2,1-d]oxazole (Preparation 43B, 123 mg, 0.298 mmol) in dichloromethane (3 mL) was added 1 M boron tribromide (1.491 mL, 1.491 mmol) in dichloromethane dropwise, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched by the slow addition of saturated ammonium chloride, extracted with dichloromethane, washed with water and brine. The combined aq. layers were back extracted with dichloromethane. The combined organic layers were dried over magnesium sulfate and evaporated to give a yellow crystalline solid (quantitative yield). 1H NMR (400 MHz, CDCl3 mixed with methanol-d4) δ ppm 7.66 (2H, d, J=6.82 Hz), 7.49-7.59 (4H, m), 7.46 (1H, d, J=8.58 Hz), 6.76-6.83 (2H, m), 3.14 (2H, t, J=7.70 Hz), 3.03 (2H, t, J=7.59 Hz).

Workup

  1. customThe reaction mixture was quenched by the slow addition of saturated ammonium chloride
  2. extractionextracted with dichloromethane
  3. washwashed with water and brine
  4. extractionThe combined aq. layers were back extracted with dichloromethane
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-8a0b4b301a32456593be10e9669f9ea5
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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