Boron tribromide → [4-(2-Chloroethoxy)phenyl](4-hydroxyphenyl)methanone

HRID 626206Notes

Reaction equation

HRID 626206 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=2)=[O:12])=[CH:7][CH:6]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[O:12])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 89656042HCID 89656042, compound

Product 1

HCID 89656364[4-(2-Chloroethoxy)phenyl](4-hydroxyphenyl)methanoneYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (4-(2-chloroethoxy)phenyl)(4-methoxyphenyl)methanone (20 g, 1.0 eq) in 150 mL CH2Cl2 was added BBr3 (52 g, 3.0 eq) dropwise at 0° C. The reaction was stirred for 4 h at rt, then quenched with 500 mL ice water. The suspension was filtered and washed with water to give the product (16 g, 85%). 1H NMR (400 MHz, DMSO-d6) δ 10.36 (s, 1H), 7.69 (dd, J=6.8 Hz, 2.0 Hz, 2H), 7.64 (dd, J=6.8 Hz, 2.0 Hz, 2H), 7.11 (dd, J=7.2 Hz, 2.0 Hz, 2H), 6.90 (dd, J=6.8 Hz, 2.0 Hz, 2H), 4.38 (t, J=5.2 Hz, 2H), 4.01 (t, J=5.2 Hz, 2H).

Workup

  1. customquenched with 500 mL ice water
  2. filtrationThe suspension was filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-c1f0854f3f52412c8046ca8c6fdd7237
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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