Hydrogen Peroxide → 4-(4-Chlorophenyl)-3-(3-bromophenyl)-2-butanol

HRID 2354499Notes

Reaction equation

HRID 2354499 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=2)[C:10](=[O:12])[CH3:11])=[CH:4][CH:3]=1.CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].[OH-].[Na+].OO>O1CCCC1.C1(C)C=CC=CC=1.CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=2)[CH:10]([OH:12])[CH3:11])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 3611392Lithium tri-s-butylborohydrideHCID 114731833-(3-Bromophenyl)-4-(4-chlorophenyl)butan-2-one

Product 1

HCID 574387144-(4-Chlorophenyl)-3-(3-bromophenyl)-2-butanol

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-chlorophenyl)-3-(3-bromophenyl)-2-butanone (1.55 kg, 4.6 mol) in tetrahydrofuran (8.4 L) at −60° C. was added L-selectride (1.0 M in tetrahydrofuran, 5.3 L, 5.3 mol), and the reaction mixture was allowed to slowly warm up to room temperature overnight. The mixture was cooled back to 0° C., and was quenched by slow addition of acetone, aqueous sodium hydroxide (2.5 N, 8.5 L, 21 mol) and 30% hydrogen peroxide (2.1 L, 21 mol). After stirig at room temperature for 13 h, the reaction mixture was diluted with toluene (30 L). The organic layer was separated, washed with water (2×12 L), and concentrated to give the title compound as an oil. 1H NMR (500 MHz, CD3OD): δ 7.40 (s, 1H), 7.30 (d, 1H), 7.28-7.10 (m, 4H), 7.04 (d, 2H), 3.98 (m, 1H), 3.12 (dd, 1H), 2.90 (dd, 1H), 2.80 (m, 1H), 1.08 (d, 3H).

Workup

  1. temperatureThe mixture was cooled back to 0° C.
  2. customThe organic layer was separated
  3. washwashed with water (2×12 L)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-76cb2c40c0c1478f903a91dabdd0c448
Source dataset
uspto-grants-2010_07
Patent number
US07754188B2

Reaction notes

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