Bromoform → [3-Bromo-5-(trifluoromethyl)phenyl]methanol

HRID 217503

Reaction equation

HRID 217503 reaction equation
N[C:2]1[CH:3]=[C:4]([CH2:12][OH:13])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.N(OC(C)(C)C)=O.C(Br)(Br)[Br:22]>>[Br:22][C:2]1[CH:3]=[C:4]([CH2:12][OH:13])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

4

Reactant 3

HCID 5558BromoformHCID 10906Tert-Butyl nitriteHCID 53414333(3-Amino-5-(trifluoromethyl)phenyl)methanol

Product 1

HCID 29919767[3-Bromo-5-(trifluoromethyl)phenyl]methanol

Conditions

Temperature
80 °C

Procedure

[3-amino-5-(trifluoromethyl)phenyl]methanol (900 mg, 4.71 mmol) (Step A, Example 24) was suspended in CHBr3 (9 mL), and t-butyl nitrite (600 μL, 5.04 mmol) was added dropwise by syringe. The reaction was heated slowly to 80° C. and was maintained at this temperature for 10 minutes. The reaction was then cooled to room temperature, diluted with hexanes (50 mL), loaded on a silica gel column, and purified with 100% hexanes to 20% EtOAc/hexanes (2 columns) to afford [3-bromo-5-(trifluoromethyl)phenyl]methanol. Rf=0.31 (25% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) δ 7.71 (s, 1H), 7.68 (s, 1H), 7.56 (s, 1H), 4.76 (d, J=5.5 Hz, 2H), 1.86 (t, J=5.7 Hz, 1H).

Workup

  1. temperaturewas maintained at this temperature for 10 minutes
  2. temperatureThe reaction was then cooled to room temperature
  3. custompurified with 100% hexanes to 20% EtOAc/hexanes (2 columns)

Sources & evidence

ORD record
ord-74cf6f234cbe43b29a1dfbd15642b98c
Source dataset
uspto-grants-2012_06
Patent number
US08193365B2

Linked notes

Loading…