Water → 2-Bromo-4-(2-hydroxyethyl)benzonitrile

HRID 1519533Notes

Reaction equation

HRID 1519533 reaction equation
[Li+].[BH4-].C[O:4][C:5](=O)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[C:9]([Br:15])[CH:8]=1.O>C1COCC1>[Br:15][C:9]1[CH:8]=[C:7]([CH2:6][CH2:5][OH:4])[CH:12]=[CH:11][C:10]=1[C:13]#[N:14]

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 77231317Methyl (3-bromo-4-cyanophenyl)acetate

Product 1

HCID 675145552-Bromo-4-(2-hydroxyethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiBH4 (1.48 mL, 2.95 mmol, 2 M in THF) was added to a stirred solution of methyl(3-bromo-4-cyanophenyl)acetate (0.50 g, 2.0 mmol) in THF (25 ml) at 0° C. The resulting solution was stirred for 12 h. Water (15 ml) was added, and the resulting solution was extracted with dichloromethane (2×50 ml). The combined organic layers were dried over MgSO4, filtered, and evaporated under reduced pressure to yield the crude product as a cloudy oil. 1H NMR (500 MHz, CDCl3) δ 7.63 (s, 1H), 7.61 (d, J=5.7, 1H), 7.33 (d, J=7.8 Hz, 1H), 3.93 (t, J=1.6, J=4.8 Hz, 2H), 2.92 (t, J=6.6, J=5.1 Hz, 2H). LC-MS (IE, m/z): 210.1 [(M+1)]+−OH].

Workup

  1. extractionthe resulting solution was extracted with dichloromethane (2×50 ml)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e7d0a9cd65b04b6fb717138bd1ddd738
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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