Carbon tetrabromide → 2-(Bromomethyl)-4-fluorophenyl difluoro[4'-(trifluoromethyl)biphenyl-4-yl]methyl ether

HRID 1672639Notes

Reaction equation

HRID 1672639 reaction equation
[F:1][C:2]([F:29])([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)[O:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[CH2:11]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:49]C(Br)(Br)Br>ClCCl>[F:1][C:2]([O:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[CH2:11][Br:49])([F:29])[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 57864335(2-{Difluoro-[4'-(trifluoromethyl)biphenyl-4-yl]methoxy}-5-fluorophenyl)methanol

Product 1

HCID 578643902-(Bromomethyl)-4-fluorophenyl difluoro[4'-(trifluoromethyl)biphenyl-4-yl]methyl etherYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

220 mg (0.53 mmol) of (2-{difluoro-[4′-(trifluoromethyl)biphenyl-4-yl]methoxy}-5-fluorophenyl)-methanol from Example 40A, 154 mg (0.59 mmol) of triphenylphosphine and 194.6 mg (0.59 mmol) tetrabromomethane are stirred in 5 ml dichloromethane at RT for 12 hours. 2 g of silica gel are added to the reaction mixture, and the mixture is then dried in vacuo and purified by silica gel chromatography (mobile phase: cyclohexane/ethyl acetate 10:1). 217 mg (0.46 mmol, 95% purity, 81% yield) of a solid are isolated.

Workup

  1. addition2 g of silica gel are added to the reaction mixture
  2. customthe mixture is then dried in vacuo
  3. custompurified by silica gel chromatography (mobile phase: cyclohexane/ethyl acetate 10:1)
  4. custom217 mg (0.46 mmol, 95% purity, 81% yield) of a solid are isolated

Sources & evidence

ORD record
ord-1d3de55fbd534dc4b671240cf700a04c
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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