Diethyl Ether → 5-Bromo-2-hydroxybenzonitrile

HRID 2228643Notes

Reaction equation

HRID 2228643 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9])#[N:2].[H+].[B-](F)(F)(F)F.CCOCC.[Br:21]N1C(=O)CCC1=O>CC#N>[OH:9][C:4]1[CH:5]=[CH:6][C:7]([Br:21])=[CH:8][C:3]=1[C:1]#[N:2]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 119072-HydroxybenzonitrileHCID 28118Tetrafluoroboric acidHCID 67184N-bromobutanimide

Product 1

HCID 27570145-Bromo-2-hydroxybenzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred, cooled (−20° C.) solution of 2-cyanophenol (30 g, 252 mmole) in dried MeCN (400 mL) was added HBF4.Et2O (45 g, 277.1 mmole), and N-bromosuccinimide (53.8 g, 302.3 mmole). After addition was completed, the mixture was warmed to RT, and stirred in 4 h. The mixture was cooled and quenched by 50% aqueous NaHSO3. The mixture was concentrated to removed excess of MeCN. The off-white solid thus obtained was filtered and dried by air (42.4 g, 85%). 1H-NMR (300 MHz, DMSO-d6): δ6.99 (d, J=8.9 Hz, 1H), 7.67 (dd, J=2.5, 8.9 Hz,1H), 7.88 (d, J=2.5 Hz,1H).

Workup

  1. additionAfter addition
  2. temperatureThe mixture was cooled
  3. customquenched by 50% aqueous NaHSO3
  4. concentrationThe mixture was concentrated
  5. customto removed excess of MeCN
  6. customThe off-white solid thus obtained
  7. filtrationwas filtered
  8. customdried by air (42.4 g, 85%)

Sources & evidence

ORD record
ord-41c48d1c737043fb86a1fe133e52e5fd
Source dataset
uspto-grants-2002_07
Patent number
US06417215B1

Reaction notes

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