4'-Bromo-4-(dimethylamino)biphenyl-2-carboxylic acid → (4'-Bromo-4-(dimethylamino)biphenyl-2-yl)methanol

HRID 1043436Notes

Reaction equation

HRID 1043436 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:17](O)=[O:18])=[CH:10][C:11]([N:14]([CH3:16])[CH3:15])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]([CH3:15])[CH3:16])=[CH:10][C:9]=2[CH2:17][OH:18])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 592665644'-Bromo-4-(dimethylamino)biphenyl-2-carboxylic acid

Product 1

HCID 59266574(4'-Bromo-4-(dimethylamino)biphenyl-2-yl)methanolYield 98%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

4′-bromo-4-(dimethylamino)biphenyl-2-carboxylic acid (1.34 g, 4.19 mmol) in THF (40 mL) was cooled to 0° C. Borane tetrahydrofuran complex (8.37 mL, 8.37 mmol) was added dropwise over 15 min. and allowed to warm up to r.t. overnight. The reaction was diluted with EtOAc and washed with water, saturated ammonium chloride, and then brine. The organic layer was dried over MgSO4, filtered and evaporated to give (4′-bromo-4-(dimethylamino)biphenyl-2-yl)methanol (1.25 g, 4.08 mmol, 98% yield) as a white solid. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 2.93-3.05 (m, 6H) 4.58 (s, 2H) 6.72 (dd, J=8.55, 2.75 Hz, 1H) 6.90 (d, J=2.75 Hz, 1H) 7.14 (d, J=8.55 Hz, 1H) 7.21-7.25 (m, 2H) 7.44-7.55 (m, 2H).

Workup

  1. additionBorane tetrahydrofuran complex (8.37 mL, 8.37 mmol) was added dropwise over 15 min.
  2. washwashed with water, saturated ammonium chloride
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-335509e11a5a4b3da569bd77234f2f19
Source dataset
uspto-grants-2013_10
Patent number
US08563505B2

Reaction notes

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