Boron tribromide → HCID 54160648, compound

HRID 1939286Notes

Reaction equation

HRID 1939286 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[C:17]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:16]=[CH:15][C:14]=2[O:26]C)=[O:11])[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br>ClCCl>[F:1][C:2]([F:28])([F:29])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[C:17]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:16]=[CH:15][C:14]=2[OH:26])=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromide2×HCID 54328699HCID 54328699, compound

Product 1

HCID 54160648HCID 54160648, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.) suspension of N-(3-(trifluoromethyl)phenyl)-N'-(2-methoxy-5-(phenylamino)phenyl) urea (1.00 g, 2.5 mmol) in dichloromethane (50 ml), boron tribromide (0.48 ml, 5.1 mmol) was added. After the addition of boron tribromide the ice bath was removed and the reaction mixture was stirred for 3 hours at RT. The reaction was poured on ice (10 ml) and 1M sodium bicarbonate (50 ml) was added. The aqueous phase was extracted with ethyl acetate (50 ml) and the organic phase dried over magnesium sulfate. 1.05 g crude product was obtained. The crude product was purified by column chromatography on silica gel using petroleum ether/ethyl acetate 1:1 as eluent. The partly purified product (0.61 g) was recrystallized from ethanol/water 1:1 (20 ml). 0.20 g (21%) of the title compound was isolated. M.p. 166°-168° C.

Workup

  1. additionwas added
  2. customwas removed
  3. additionThe reaction was poured on ice (10 ml) and 1M sodium bicarbonate (50 ml)
  4. additionwas added
  5. extractionThe aqueous phase was extracted with ethyl acetate (50 ml)
  6. dry with materialthe organic phase dried over magnesium sulfate
  7. custom1.05 g crude product was obtained
  8. customThe crude product was purified by column chromatography on silica gel
  9. customThe partly purified product (0.61 g) was recrystallized from ethanol/water 1:1 (20 ml)

Sources & evidence

ORD record
ord-0478d1d03b2d40daab57270d5150970b
Source dataset
uspto-grants-1997_12
Patent number
US05696138

Reaction notes

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